CN1551885A - Cyclic indole and heteroindole derivatives, the production and use thereof as medicaments - Google Patents
Cyclic indole and heteroindole derivatives, the production and use thereof as medicaments Download PDFInfo
- Publication number
- CN1551885A CN1551885A CNA028172639A CN02817263A CN1551885A CN 1551885 A CN1551885 A CN 1551885A CN A028172639 A CNA028172639 A CN A028172639A CN 02817263 A CN02817263 A CN 02817263A CN 1551885 A CN1551885 A CN 1551885A
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- Prior art keywords
- alkyl
- branched
- straight
- group
- unsubstituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003814 drug Substances 0.000 title claims abstract description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract 2
- 125000004122 cyclic group Chemical group 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 24
- -1 nitro, hydroxyl Chemical group 0.000 claims description 24
- 150000002576 ketones Chemical class 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 239000002585 base Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 13
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003574 free electron Substances 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 210000004027 cell Anatomy 0.000 description 31
- 239000002994 raw material Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 18
- 150000002475 indoles Chemical class 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
- 230000022131 cell cycle Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 230000001028 anti-proliverative effect Effects 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- QNRXNRGSOJZINA-UHFFFAOYSA-N indoline-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)CC2=C1 QNRXNRGSOJZINA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000007912 intraperitoneal administration Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003810 ethyl acetate extraction Methods 0.000 description 5
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229940091250 magnesium supplement Drugs 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 210000004881 tumor cell Anatomy 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 230000035479 physiological effects, processes and functions Effects 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- LQGNCUXDDPRDJH-UHFFFAOYSA-N 3'-GMP Natural products C1C(O)C(O)CC2(C)C(C(O)CC3(C(C(C)(O)C(O)CCC(C)C)CCC33O)C)C3=CC(=O)C21 LQGNCUXDDPRDJH-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- LRJUYAVTHIEHAI-UHFFFAOYSA-N Muristeron A Natural products C1C(O)C(O)CC2(C)C(C(O)CC3(C(C(C)(O)C(O)CCC(C)C)CCC33O)C)C3=CC(=O)C21O LRJUYAVTHIEHAI-UHFFFAOYSA-N 0.000 description 2
- LRJUYAVTHIEHAI-LHBNDURVSA-N Muristerone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H]([C@H](O)C[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)C)CC[C@]33O)C)C3=CC(=O)[C@@]21O LRJUYAVTHIEHAI-LHBNDURVSA-N 0.000 description 2
- 241000699660 Mus musculus Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DXGTUUQHTDOFFQ-UHFFFAOYSA-N [N].C1=CC=C2NC=CC2=C1 Chemical group [N].C1=CC=C2NC=CC2=C1 DXGTUUQHTDOFFQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000007541 cellular toxicity Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 2
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 2
- NAQQTJZRCYNBRX-UHFFFAOYSA-N n-pentan-3-ylidenehydroxylamine Chemical compound CCC(CC)=NO NAQQTJZRCYNBRX-UHFFFAOYSA-N 0.000 description 2
- 238000011580 nude mouse model Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000820 toxicity test Toxicity 0.000 description 2
- XVGVNOVEJAWYEO-UHFFFAOYSA-N 3,4-dihydro-2h-oxadiazine Chemical compound C1NNOC=C1 XVGVNOVEJAWYEO-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241001132374 Asta Species 0.000 description 1
- 229940123587 Cell cycle inhibitor Drugs 0.000 description 1
- 101000983970 Conus catus Alpha-conotoxin CIB Proteins 0.000 description 1
- 101000932768 Conus catus Alpha-conotoxin CIC Proteins 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- UPEZCKBFRMILAV-JNEQICEOSA-N Ecdysone Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@H]([C@@H](O)CCC(O)(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 UPEZCKBFRMILAV-JNEQICEOSA-N 0.000 description 1
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 1
- 230000010190 G1 phase Effects 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical class Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- IZFMMUBPBGYYCI-UHFFFAOYSA-N [Mg]C1=CC=C(Cl)C=C1 Chemical compound [Mg]C1=CC=C(Cl)C=C1 IZFMMUBPBGYYCI-UHFFFAOYSA-N 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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- UPEZCKBFRMILAV-JMZLNJERSA-N ecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H]([C@H](O)CCC(C)(C)O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 UPEZCKBFRMILAV-JMZLNJERSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
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- 150000002460 imidazoles Chemical class 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
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- SNHOZPMHMQQMNI-UHFFFAOYSA-N lithium;2h-thiophen-2-ide Chemical compound [Li+].C=1C=[C-]SC=1 SNHOZPMHMQQMNI-UHFFFAOYSA-N 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- AMQFJJCJOSCKNY-UHFFFAOYSA-N methyl hydrogen sulfate;pyrazine Chemical compound COS(O)(=O)=O.C1=CN=CC=N1 AMQFJJCJOSCKNY-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D515/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D515/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D515/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D515/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention relates to novel, substituted, fused indole and heteroindole derivatives of the general formula I their tautomers, stereoisomers, mixtures and pharmaceutically acceptable salts, their synthesis and their use as pharmaceuticals, especially as anti-tumor agents, for mammals, especially for man.
Description
The present invention relates to the indoles and the assorted indole derivatives of the novel substituted of formula I
Its tautomer, its steric isomer, its mixture and its pharmacy acceptable salt also relate to its preparation and purposes as medicine, especially as antineoplastic agent, are used for Mammals, and be particularly human.
The German patent application on April 28th, 2000 (Patent ASTA Medica AG withPrivatdozent Dr.Mahboobi) has been described the method for preparing the 2-acyl indol via the 2-lithium indoles of correspondence.
Theophil Eicher and Ralph Rohde, Synthesis 1985, and pp.619-625 has described 1, the preparation of 2-phenylbenzene-3a-azepine cyclopenta [a] indenes-3-ketone.Both there be not the open medical applications of described compound of yet not pointing out.
According to one aspect of the present invention, formula I is provided compound, or its tautomer, steric isomer, mixture or pharmacy acceptable salt:
Wherein
R1 is a hydrogen, (C6-C14)-aryl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, (C1-C13)-heteroaryl---it contains at least one to four N, NH, O and/or S are as ring members and be unsubstituted or replaced wholly or in part by identical or different substituting group, (C3-C8)-cycloalkyl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, perhaps straight or branched (C1-C20)-alkyl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group;
A, B, C or D be nitrogen-atoms or the carbon atom for being replaced by R2-R5 independently of one another;
R2, R3, R4 and R5 are free electron to (if the bonding companion is A independently of one another, B, C or D are nitrogen-atoms), hydrogen, halogen, cyano group, nitro, hydroxyl, straight or branched (C1-C6)-alkyl, straight or branched (the C1-C6)-alkyl that is replaced by one or more halogen atoms, straight or branched (C1-C6)-alkoxyl group, straight or branched (the C1-C6)-alkoxyl group that is replaced by one or more halogen atoms, straight or branched (C1-C6)-alkylene dioxo base, (C1-C6)-the alkyl-carbonyl oxygen base, (C1-C6)-alkoxy-carbonyl oxy, (C1-C6)-alkylthio, (C1-C6)-alkyl sulphinyl, (C1-C6)-alkyl sulphonyl, carboxyl, (C1-C6)-alkyl carboxylic acid ester, acid amides, N-(C1-C6)-alkylamide, N, N-two-(C1-C6)-alkylamide, (C1-C6)-alkoxyl group-(C1-C6)-alkyl, amino, single-(C1-C6)-alkylamino, two-(C1-C6)-alkylamino---wherein two (C1-C6) groups can constitute optional one or more NH that contain together, N-(C1-C6)-alkyl, the ring of O or S, (C6-C14)-aryl, (C6-C14)-aryloxy, (C6-C14)-aryl-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C6)-alkoxyl group-(C1-C6)-alkyl, (C1-C6)-alkyl-carbonyl, (C1-C6)-alkoxy carbonyl, hydroxyl, wherein the group of two direct neighbors can be connected to each other;
R6 is (C6-C14)-aryl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, (C1-C13)-heteroaryl---it contains at least one to four N, NH, O and/or S are as ring members and be unsubstituted or replaced wholly or in part by identical or different substituting group, (C3-C8)-cycloalkyl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, straight or branched (C1-C20)-alkyl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group that wherein identical or different substituting group is selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, hydroxyl, (C1-C6)-alkyl, (C1-C6)-alkoxyl group, carboxyl, (the C1-C6)-alkyl that is replaced by one or more identical or different halogen atoms, (the C1-C6)-alkoxyl group that is replaced by one or more identical or different halogen atoms, straight or branched (C2-C6)-thiazolinyl, straight or branched (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, straight or branched (C1-C6)-alkoxyl group, straight or branched (C1-C6)-alkylene dioxo base, (C1-C6)-alkoxyl group-(C1-C6)-alkyl, (C6-C14)-aryl, (C6-C14)-aryl-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C4)-alkoxyl group-(C1-C6)-alkyl;
X is carbonyl (C=O), sulfoxide (S=O) or alkylsulfonyl (SO
2);
Y is Sauerstoffatom or the nitrogen-atoms (NR7) that replaced by radicals R 7, wherein
R7 is (C6-C14)-aryl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, (C1-C13)-heteroaryl---it contains at least one to four N, NH, O and/or S are as ring members and be unsubstituted or replaced wholly or in part by identical or different substituting group, (C3-C8)-cycloalkyl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, straight or branched (C1-C20)-alkyl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group that wherein identical or different substituting group is selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, hydroxyl, (C1-C6)-alkyl, (C1-C6)-alkoxyl group, carboxyl, (the C1-C6)-alkyl that is replaced by one or more identical or different halogen atoms, (the C1-C6)-alkoxyl group that is replaced by one or more identical or different halogen atoms, straight or branched (C2-C6)-thiazolinyl, straight or branched (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, straight or branched (C1-C6)-alkoxyl group, straight or branched (C1-C6)-alkylene dioxo base, (C1-C6)-alkoxyl group-(C1-C6)-alkyl, the straight or branched list-(C1-C6)-alkylamino, straight or branched two-(C1-C6)-alkylamino---wherein two (C1-C4) groups can constitute optional one or more NH that contain together, N-(C1-C6)-alkyl, the ring of O or S, (C6-C14)-aryl, (C6-C14)-aryl-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C4)-alkoxyl group-(C1-C6)-alkyl, (C1-C6)-alkyl-carbonyl, (C1-C6)-alkoxy carbonyl;
N is 0 or 1, and its condition is if n=0, so
The carbon atom that Z is replaced by radicals R 8 (C-R8), wherein
R8 is (C6-C14)-aryl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, (C1-C13)-heteroaryl---it contains at least one to four N, NH, O and/or S are as ring members and be unsubstituted or replaced wholly or in part by identical or different substituting group, (C3-C8)-cycloalkyl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, straight or branched (C1-C20)-alkyl---it is unsubstituted or is replaced wholly or in part by identical or different substituting group, wherein identical or different substituting group is selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, hydroxyl, (C1-C6)-alkyl, (C1-C6)-alkoxyl group, carboxyl, (the C1-C6)-alkyl that is replaced by one or more identical or different halogen atoms, (the C1-C6)-alkoxyl group that is replaced by one or more identical or different halogen atoms, straight or branched (C2-C6)-thiazolinyl, straight or branched (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, straight or branched (C1-C6)-alkoxyl group, straight or branched (C1-C6)-alkylene dioxo base, straight or branched (C1-C6)-alkylthio, (C1-C4)-alkyl sulphinyl, (C1-C4)-alkyl sulphonyl, (C6-C14)-arylthio, (C6-C14)-aryl sulfonyl kia, (C6-C14)-aryl sulfonyl, (C1-C6)-alkoxyl group-(C1-C6)-alkyl, the straight or branched list-(C1-C6)-alkylamino, straight or branched two-(C1-C6)-alkylamino---wherein two (C1-C4) groups can constitute optional one or more NH that contain together, N-(C1-C6)-alkyl, the ring of O or S, (C6-C14)-aryl, (C6-C14)-aryloxy, (C6-C14)-aryl-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C4)-alkoxyl group-(C1-C6)-alkyl, (C1-C6)-alkyl-carbonyl, (C1-C6)-alkoxy carbonyl, straight or branched list-N-(C1-C6)-alkyl-carbonyl-amino, straight or branched two-N, N-(C1-C6)-alkyl-carbonyl-amino, straight or branched list-N-(C1-C6)-alkoxycarbonyl amino, straight or branched two-N, N-(C1-C6)-alkoxycarbonyl amino, straight or branched N-(C1-C6)-alkyl-carbonyl-amino-N-(C1-C6)-alkylamino, straight or branched N-(C1-C6)-alkoxycarbonyl amino-N-(C1-C6)-alkylamino;
And if n=1, so
Z is a nitrogen-atoms.
Advance on the one hand according to of the present invention, such compound is provided, it is characterized in that R1 is a hydrogen, R2, R3, R4 and R5 are hydrogen independently of one another, halogen or (C1-C6)-alkoxyl group, R6 is that straight or branched (C1-C20)-alkyl-it is unsubstituted or is replaced wholly or in part by identical or different substituting group, or (C6-C14)-aryl-it is unsubstituted or is replaced wholly or in part by identical or different substituting group, its substituting group is selected from (C1-C6)-alkoxyl group and halogen, Y is Sauerstoffatom or group N-R7, wherein R7 is that (C6-C14)-aryl-it is unsubstituted or is replaced wholly or in part by identical or different substituting group, X is carbonyl (C=O), Z is a nitrogen-atoms, n=1.
Advance on the one hand according to of the present invention, such compound is provided, it is characterized in that R1 is a hydrogen, R2, R3, R4 and R5 are hydrogen independently of one another, halogen or (C1-C6)-alkoxyl group, R6 is that straight or branched (C1-C20)-alkyl-it is unsubstituted or is replaced wholly or in part by identical or different substituting group, or (C6-C14)-aryl-it is unsubstituted or is replaced wholly or in part by identical or different substituting group, its substituting group is selected from (C1-C6)-alkoxyl group and halogen, n=0, Z is group C-R8, wherein R8 is that (C6-C14)-aryl-it is unsubstituted or is replaced wholly or in part by identical or different substituting group, its substituting group is selected from (C1-C6)-alkoxyl group and halogen, and X is carbonyl (C=O).
Advance on the one hand according to of the present invention, provide according to above-claimed cpd of the present invention as medicine.
Advance on the one hand according to of the present invention, provide above-claimed cpd according to the present invention to be used to control Mammals, the particularly purposes of human tumor illness.
Advance on the one hand according to of the present invention, medicine is provided, it comprises at least a according to above-claimed cpd of the present invention and pharmaceutically acceptable auxiliary, thinner and/or carrier.
Advance on the one hand according to of the present invention, the method for preparation according to formula I compound of the present invention be provided,
Wherein A, B, C, D, R1, R2, R3, R4, R4, R5, X, Y, Z and n are defined as claim 1, it is characterized in that
A) make following formula ketone
With aa) oxime or bb) hydrazine derivative H2N-NH-R7 reaction, wherein R7 is defined as claim 1, makes products therefrom and activatory carbonyl, sulfoxide or sulfonyl-derivatives cyclisation,
Perhaps with cc) phenyl acetic acid derivatives X1-CO-CH2-R8 reaction, wherein X1 is the leavings group that is fit to, for example halogen or (C1-C2)-alkoxyl group, and R8 be such as claim 1 definition, cyclisation in the presence of alkali then.
Can obtain by known method itself according to formula I compound of the present invention.The method that is fit to for example has following method:
If a) make and possess---suitably---indoles of the nucleofugicity leavings group E of Shi Heing or assorted benzazolyl compounds and organometallic compound reaction:
Wherein
R1, R2, R3, R4, R5, R6, A, B, C and D are as defined at first,
R9 is hydrogen, straight or branched (C1-C6)-alkyl-carbonyl---it be unsubstituted or by one or more halogen atom replacements, straight or branched (C1-C6)-alkoxy carbonyl, replacement (C6-C14)-aryl-(C1)-alkyl, straight or branched (C1-C6)-alkyl sulphonyl or (C6-C14)-aryl sulfonyl---, and it is unsubstituted or is replaced by (C1-C6)-alkyl
E is OH, halogen atom---for example fluorine, chlorine or bromine atom, (C1-C6)-alkoxyl group, imidazoles and M are Li, Mg-R10,
Wherein R10 is a halogen atom, for example chlorine, bromine or iodine atom;
With regard to n=0:
B1) make 2-acyl indol or assorted benzazolyl compounds and have the reagent react of suitable nucleofugicity leavings group, if suitably simultaneously or remove substituent R 9 on the indole nitrogen atom before:
Wherein
R1, R2, R3, R4, R5, R6, R8, R9, A, B, C, D, E and X are as defined at first,
C1) make 2-acyl indol or assorted benzazolyl compounds and alkali reaction, preferred sodium hydride:
Wherein
R1, R2, R3, R4, R5, R6, R8, A, B, C, D and X are as defined at first, and the carbon atom that replaced by radicals R 8 of Z;
With regard to n=1:
B2) make 2-acyl indol or assorted benzazolyl compounds and primary amino derivatives reaction unsubstituted or that replace:
Wherein
R1; R2; R3; R4; R5; R6; R9; A; B; C; D and Y are as defined at first; Z is a nitrogen-atoms; and R10 is a hydrogen; straight or branched (C1-C6)-alkyl; straight or branched (the C1-C6)-alkyl that is replaced by one or more halogen atoms; straight or branched (the C1-C6)-alkoxyl group that is replaced by one or more halogen atoms; (C2-C6)-thiazolinyl; (C2-C6)-alkynyl; (C3-C8)-cycloalkyl; (C1-C6)-alkyl-carbonyl; (C1-C6)-alkoxy carbonyl; (C1-C6)-alkyl sulphinyl; (C1-C6)-alkyl sulphonyl; (C1-C6)-alkoxyl group-(C1-C6)-alkyl; (C6-C14)-aryl; (C6-C14)-aryl-(C1-C6)-alkyl; (C6-C14)-aryl-(C1-C6)-alkoxyl group-(C1-C6)-alkyl; (C1-C6)-alkyl-carbonyl; (C1-C6)-alkoxy carbonyl
C2) make indoles or assorted benzazolyl compounds and have the reagent react of suitable nucleofugicity leavings group, if suitably simultaneously or remove substituent R 9 on the indole nitrogen atom before:
Wherein
R1, R2, R3, R4, R5, R6, R9, A, B, C, D and X are that Z is a nitrogen-atoms as defined at first, and R10 is a hydrogen atom;
R11 and R12 are the nucleofugicity leavings group independently of one another, halogen atom for example, and for example chlorine, bromine or iodine atom, (C1-C6)-alkoxyl group or N-acyl imidazoles (imidazolide).
But, it is particularly advantageous being prepared like this, make indoles or the sharp refined reagent react of assorted indoles formylimidazoles (heteroindolecarboximidazolide) dative of isolating or generated in-situ formula II,
Wherein
R1, R2, R3, R4, R5, R9, A, B, C and D are as defined at first, make formula III indoles or assorted indole derivatives and azanol reaction,
Wherein
R1, R2, R3, R4, R5, R6, R9, A, B, C and D are as defined at first,
Make indoles or assorted indole derivatives and the N of formula IV, N '-carbonyl dimidazoles cyclisation obtains indoles or the assorted indole derivatives of formula V
Wherein
R1, R2, R3, R4, R5, R6, A, B, C and D are as defined at first,
And in the presence of alkali, for example sodium hydride makes indoles or the assorted indole derivatives and the phenyl acetyl halide cyclisation unsubstituted or that replace of above-mentioned formula III, obtains indoles or the assorted indole derivatives of formula VI
Wherein
R1, R2, R3, R4, R5, R6, A, B, C and D are that R9 is a hydrogen atom as defined at first.
Compound as raw material is commercial available or known from document a bit, obtains by known method from document; In addition, its preparation has been described in an embodiment.Known method for example is described in L.and M.Fieser from document, OrganischeChemie[Organic Chemistry], 2nd edition, the document of quoting on 1979, the 1417-1483 pages or leaves and the 1481-1483 page or leaf; Houben-Weyl-M ü ller, Methodender organischen Chemie [Methods of organic chemistry] and Ullmanns Encyklopadie der technischen Chemie[Ullmann ' sEncyclopedia of Technical Chemistry] in.
In addition, gained formula I compound can be separated into its enantiomorph and/or diastereomer.Thereby for example, the gained formula I compound that exists with racemic object form can be separated into its enantiomorph by known method itself, and the formula I compound with at least 2 unsymmetrical carbons is because its physical chemistry difference, can be separated into its diastereomer by known method itself, for example chromatography and/or fractional crystallisation method, when obtaining racemic form, can be separated into enantiomorph as mentioned above.
Separation of Enantiomers preferably is performed such, separates by chirality being carried out mutually column chromatography, and perhaps recrystallization from the solvent of optically active, perhaps with the optically active substance reaction, the latter and racemic compound generation salt or derivative, for example ester or acid amides.
In addition, gained formula I compound can be converted into its salt, particularly with regard to pharmaceutical application, be converted on its pharmacology and physiology on acceptable salt, wherein use inorganic or organic acid.The acid that is suitable for this purpose for example has hydrochloric acid, Hydrogen bromide, sulfuric acid, phosphoric acid, fumaric acid, succsinic acid, lactic acid, citric acid, tartrate or toxilic acid.
And, if contain acidic-group, carboxyl for example, formula I compound can---if necessary---be converted into its salt, particularly with regard to pharmaceutical application, be converted into acceptable salt on its physiology, wherein use inorganic or organic bases.The alkali that is suitable for this purpose for example has sodium hydroxide, potassium hydroxide, hexahydroaniline, thanomin, diethanolamine and trolamine.
Below, elaborate the present invention by embodiment; But, the invention is not restricted to these embodiment.
Preparation is according to the general technology of 2-acyl indol of the present invention
Method A) separating imidazoles-1-base (1H-indoles-2-yl) ketone also reacts with organometallic reagent subsequently
When stirring, at room temperature, go through 60 minutes with 72mmol (11.67g, 1.2 equivalents) N, the 250ml tetrahydrofuran solution of N '-carbonyl dimidazoles is added drop-wise in the 200ml tetrahydrofuran solution of 60mmol (11.47g) 5-methoxyl group Indoline-2-carboxylic acid.Further stir after 15 minutes, utilize rotatory evaporator to remove and desolvate, make resistates from the 220ml tetrahydrofuran (THF): recrystallization the solution of hexane=3: 2.Obtain imidazoles-1-base-(5-methoxyl group-1H-indoles-2-yl) ketone, be orange-brown solid.
M.p.:>300 (decomposition)
Under 0 ℃, 2.2 equivalent organometallic compounds are added drop-wise in the tetrahydrofuran solution (3ml/mmol) of 1 equivalent imidazoles-1-base-(5-methoxyl group-1H-indoles-2-yl) ketone, so that internal temperature is no more than 5 ℃.(mobile phase is an ethyl acetate: hexane=1: 1) by the conversion of tlc monitoring reaction.Reaction adds entry (10ml/mmol) to reaction soln after finishing, and regulates pH to 6 with concentrated hydrochloric acid.Separate organic phase, water ethyl acetate extraction three times (each 2ml/mmol).Merge organic phase,, utilize rotatory evaporator to remove and desolvate, make resistates crystallization from alcohol through dried over mgso.
Embodiment A 1:
Reagent A 1: methylmagnesium-chloride, 3.0M tetrahydrofuran solution
1-(5-methoxyl group-1H-indoles-2-yl) ethyl ketone
M.p.:164-167 ℃ (2-propyl alcohol)
Embodiment A 2:
Reagent A 2: phenyl-magnesium-bromide, 3.0M diethyl ether solution
(5-methoxyl group-1H-indoles-2-yl) phenyl ketone
M.p.:164-166 ℃ (propyl carbinol)
Embodiment A 3:
Reagent A 3: bromination 3-p-methoxy-phenyl magnesium, 1.0M tetrahydrofuran solution
(5-methoxyl group-1H-indoles-2-yl)-(3-p-methoxy-phenyl) ketone
M.p.:143-145 ℃ (propyl carbinol)
Embodiment A 4:
Reagent A 4: bromination 4-p-methoxy-phenyl magnesium, 0.5M tetrahydrofuran solution
(5-methoxyl group-1H-indoles-2-yl)-(4-p-methoxy-phenyl) ketone
M.p.:155-158 ℃ (propyl carbinol)
Embodiment A 5:
Reagent A 5: bromination 4-chloro-phenyl-magnesium, 1.0M diethyl ether solution
(4-chloro-phenyl-)-(5-methoxyl group-1H-indoles-2-yl) ketone
M.p.:190-192 ℃ (propyl carbinol)
Embodiment A 6:
Reagent A 6:2-thienyl lithium, the 1.0M tetrahydrofuran solution
(5-methoxyl group-1H-indoles-2-yl) thiophene-2-base ketone
M.p.:152-154 ℃ (propyl carbinol)
Method B) pot process: synthetic imidazoles-1-base (1H-indoles-2-yl) ketone and original position and organometallic reagent reaction subsequently
When stirring, under inert atmosphere, at room temperature, go through 20 minutes with 26mmol (1.05 equivalent) N, the tetrahydrofuran solution of N '-carbonyl dimidazoles (3ml/mmol) is added drop-wise in the tetrahydrofuran solution (2ml/mmol) of 25mmol Indoline-2-carboxylic acid.Further stir after 60 minutes, reaction soln is cooled to 0 ℃, drip 3.5 equivalent organometallic compounds, so that internal temperature is no more than 5 ℃ (about 60 minutes).(mobile phase is an ethyl acetate: hexane=1: 1) by the conversion of tlc monitoring reaction.Reaction adds entry (10ml/mmol) to reaction soln after finishing, and regulates pH to 6 with concentrated hydrochloric acid.Separate organic phase, water ethyl acetate extraction three times (each 2ml/mmol).Merge organic phase,, utilize rotatory evaporator to remove and desolvate, make resistates crystallization from alcohol through dried over mgso.
Embodiment B 1:
Raw material: Indoline-2-carboxylic acid
Reagent B1: bromination 2-p-methoxy-phenyl magnesium, 1.0M tetrahydrofuran solution
(1H-indoles-2-yl)-(2-p-methoxy-phenyl) ketone
M.p.:129-130 ℃ of (ethanol: water=4: 1)
Embodiment B 2:
Raw material: Indoline-2-carboxylic acid
Reagent A 3: bromination 3-p-methoxy-phenyl magnesium, 1.0M tetrahydrofuran solution
(1H-indoles-2-yl)-(3-p-methoxy-phenyl) ketone
M.p.:119-121 ℃ (2-propyl alcohol)
Embodiment B 3:
Raw material: 5-methoxyl group Indoline-2-carboxylic acid
Reagent A 1: methylmagnesium-chloride, 3.0M tetrahydrofuran solution
1-(5-methoxyl group-1H-indoles-2-yl) ethyl ketone
M.p.:164-167 ℃ (2-propyl alcohol)
Embodiment B 4:
Raw material: 5-methoxyl group Indoline-2-carboxylic acid
Reagent B4: ethyl-magnesium-chloride, 3.0M tetrahydrofuran solution
1-(5-methoxyl group-1H-indoles-2-yl) third-1-ketone
M.p.:173-175 ℃ (2-propyl alcohol)
Embodiment B 5:
Raw material: 5-methoxyl group Indoline-2-carboxylic acid
Reagent A 2: phenyl-magnesium-bromide, 3.0M diethyl ether solution
(5-methoxyl group-1H-indoles-2-yl) phenyl ketone
M.p.:164-166 ℃ (propyl carbinol)
Embodiment B 6:
Raw material: 5-methoxyl group Indoline-2-carboxylic acid
Reagent A 3: bromination 3-p-methoxy-phenyl magnesium, 1.0M tetrahydrofuran solution
(5-methoxyl group-1H-indoles-2-yl)-(3-p-methoxy-phenyl) ketone
M.p.:143-145 ℃ (propyl carbinol)
Preparation is according to the general technology of oxa-diaza of the present invention (oxadiaza) derivative
Method C) preparation, separation and purifying indoles-2-base oxime and subsequently with N, N '-carbonyl dimidazoles reaction
C1) indoles-2-base oxime is general synthetic:
1.5 equivalent solid hydroxylamine hydrochlorides are joined in the ethanol suspension (10ml/mmol) of 1 equivalent according to the 2-acyl indol of method A or B preparation, when stirring, go through the 0.5M methanol solution that dripped 3.0 Equivalent Hydrogen potassium oxides in 5 minutes then.With reaction soln 3-9 hour (monitoring) of heating under refluxing with TLC, be cooled to room temperature after, pour into (150ml/mmol) in the water, regulate pH to 6 with hydrochloric acid (10% aqueous solution).Separate the precipitation that is generated, recrystallization from alcohol/water.If precipitation generates, then separate organic phase, water ethyl acetate extraction three times (each 2ml/mmol), merge organic phase,, utilize rotatory evaporator to remove and desolvate through dried over mgso, by the recrystallization purifying product, perhaps make crude product subsequently according to further reaction of C2 (method D).
Embodiment C 1.1 (D-81687):
Raw material A 1:1-(5-methoxyl group-1H-indoles-2-yl) ethyl ketone
1-(5-methoxyl group-1H-indoles-2-yl) ethyl ketone oxime
M.p.:148-150 ℃ (2-propyl alcohol)
Embodiment C 1.2 (D-81690):
Raw material B4:1-(5-methoxyl group-1H-indoles-2-yl) third-1-ketone
1-(5-methoxyl group-1H-indoles-2-yl) third-1-ketoxime
M.p.:163-165 ℃ (2-propyl alcohol)
Embodiment C 1.3 (D-70258):
Raw material A 2:(5-methoxyl group-1H-indoles-2-yl) phenyl ketone
(5-methoxyl group-1H-indoles-2-yl) phenyl ketone oxime
M.p.:150-152 ℃ of (2-propyl alcohol: water=2: 3)
Embodiment C 1.4 (D-70745):
Raw material A 5:(4-chloro-phenyl-)-(5-methoxyl group-1H-indoles-2-yl) ketone
(4-chloro-phenyl-)-(5-methoxyl group-1H-indoles-2-yl) ketoxime
Crude product (HPLC purity: 81%)
C2) 1H-indoles-2-base ketoxime and N, the reaction of N '-carbonyl dimidazoles:
With 1.2 equivalent solid N, N '-carbonyl dimidazoles joins in the tetrahydrofuran solution (30ml/mmol) of 1 equivalent 1H-indoles-2-base ketoxime, with mixture 1-3 hour (monitoring with TLC) of heating under refluxing.After being cooled to room temperature, pour reaction soln in the water (400ml/mmol), separate the precipitation that is generated, crystallization from alcohol.If precipitation generates, then separate organic phase, water ethyl acetate extraction three times (each 2ml/mmol).Merge organic phase, through dried over mgso, utilize rotatory evaporator to remove then and desolvate, product under atmospheric pressure passes through silica gel chromatography, and (mobile phase is an ethyl acetate: hexane=1: 3).
Embodiment C 2.1 (D-81688):
Raw material C1.1:1-(5-methoxyl group-1H-indoles-2-yl) ethyl ketone oxime
The 3-methyl isophthalic acid, 2, the 5-oxadiazine is [4,5-a] (5-methoxyl group indoles)-6-ketone also
M.p.:217-220 ℃ (2-propyl alcohol)
Embodiment C 2.2 (D-81691):
Raw material C1.2:1-(5-methoxyl group-1H-indoles-2-yl) third-1-ketoxime
3-ethyl-1,2,5-oxadiazine be [4,5-a] (5-methoxyl group indoles)-6-ketone also
M.p.:208-212 ℃ (propyl carbinol)
Embodiment C 2.3 (D-70260):
Raw material C1.3:(5-methoxyl group-1H-indoles-2-yl) phenyl ketone oxime
3-phenyl-1,2,5-oxadiazine be [4,5-a] (5-methoxyl group indoles)-6-ketone also
M.p.:198-200 ℃ (propyl carbinol)
Method D) prepared 1H-indoles-2-base ketoxime directly and N, N '-carbonyl dimidazoles reaction
According to the synthetic following oxa-diaza derivatives of technology C1, but need not purifying further reacts according to C2.
Embodiment D1 (D-81362):
Raw material B1:(1H-indoles-2-yl)-(2-p-methoxy-phenyl) ketone
3-(2-p-methoxy-phenyl)-1,2,5-oxadiazine be [4,5-a] indoles-6-ketone also
M.p.:160-162 ℃ (column chromatography)
Embodiment D2 (D-81361):
Raw material B2:(1H-indoles-2-yl)-(3-p-methoxy-phenyl) ketone
3-(3-p-methoxy-phenyl)-1,2,5-oxadiazine be [4,5-a] indoles-6-ketone also
M.p.:129-130 ℃ (column chromatography)
Embodiment D3 (D-81462):
Raw material A 3:(5-methoxyl group-1H-indoles-2-yl)-(3-p-methoxy-phenyl) ketone
3-(3-p-methoxy-phenyl)-1,2,5-oxadiazine be [4,5-a] (5-methoxyl group indoles)-6-ketone also
M.p.:171-173 ℃ (ethanol)
Embodiment D4 (D-70744):
Raw material A 5:(4-chloro-phenyl-)-(5-methoxyl group-1H-indoles-2-yl) ketone
3-(4-chloro-phenyl-)-1,2,5-oxadiazine be [4,5-a] (5-methoxyl group indoles)-6-ketone also
M.p.:227-230 ℃ (propyl carbinol)
According to above-mentioned synthesis technique C and D, can also prepare according to following compounds of the present invention (embodiment 1 to 324), from having the indole-2-carboxylic acid derivatives of different substituents:
Raw material:
Product (n=1, Z=N):
Embodiment 1 to 324:
No. | ?A | ?C | ?D | ?R | ?R1 | ?R6 | ?X | Y |
?1 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?C(O) | O |
?2 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?C(O) | O |
?3 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?C(O) | O |
?4 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?5 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?6 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?7 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?8 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?9 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?10 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?CH 3 | ?C(O) | O |
?11 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?C 2H 5 | ?C(O) | O |
?12 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?C 6H 5 | ?C(O) | O |
?13 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?14 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?C(O) | O |
?15 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?16 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?17 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?18 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?19 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?20 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?21 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?22 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?23 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?24 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?25 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?26 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?27 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?28 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?C(O) | O |
?29 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?C(O) | O |
?30 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?C(O) | O |
?31 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?32 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?C(O) | O |
?33 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?34 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?35 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?36 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?37 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?38 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?39 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?C(O) | O |
?40 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?C(O) | O |
?41 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?C(O) | O |
?42 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?43 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?C(O) | O |
?44 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?45 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?46 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?47 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?48 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?49 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?50 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?C(O) | O |
?51 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) | O |
?52 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) | O |
?53 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?54 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) | O |
?55 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?56 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?57 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?58 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?59 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?60 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?61 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?C(O) | O |
?62 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?C(O) | O |
?63 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?C(O) | O |
?64 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?65 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) | O |
?66 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?67 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?68 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?69 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?70 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?71 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?72 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?C(O) | O |
?73 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?C(O) | O |
?74 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?C(O) | O |
?75 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?76 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C(O) | O |
?77 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?78 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?79 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?80 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?81 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?82 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?83 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?C(O) | O |
?84 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?C(O) | O |
?85 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?C(O) | O |
?86 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?87 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C(O) | O |
?88 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C(O) | O |
?89 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?90 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?91 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?92 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?93 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?94 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?C(O) | O |
?95 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?C(O) | O |
?96 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ?C(O) | O |
?97 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C(O) | O |
?98 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C(O) | O |
?99 | ?CH | ?CH | ?N | ?H | ?H | 4-(CH 3O)-C 6H 4 | ?C(O) | O |
?100 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?101 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?102 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?103 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) | O |
?104 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) | O |
?105 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?S(O) | O |
?106 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?S(O) | O |
?107 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?S(O) | O |
?108 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?109 | ?CH | ?CH | ?CH | ?H | H | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?110 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?111 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?112 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?113 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?114 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?115 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?116 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?CH 3 | ?S(O) | O |
?117 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?C 2H 5 | ?S(O) | O |
?118 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?C 6H 5 | ?S(O) | O |
?119 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?120 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?121 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?122 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?123 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?124 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?125 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?126 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?127 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?S(O) | O |
?128 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?S(O) | O |
?129 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?S(O) | O |
?130 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?131 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?132 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?133 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?134 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?135 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?136 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?137 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?138 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?S(O) | O |
?139 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?S(O) | O |
?140 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?S(O) | O |
?141 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?142 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?143 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?144 | ?CH | ?C | ?CH | ?6-F | ?H | 2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?145 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?146 | ?CH | ?C | ?CH | ?6-F | ?H | 3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?147 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?148 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?149 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?S(O) | O |
?150 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?S(O) | O |
?151 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?S(O) | O |
?152 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?153 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?154 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?155 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?156 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?157 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?158 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?159 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?160 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?S(O) | O |
?161 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?S(O) | O |
?162 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?S(O) | O |
?163 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?164 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?165 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?166 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?167 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?168 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?169 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?170 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?171 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?S(O) | O |
?172 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?S(O) | O |
?173 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?S(O) | O |
?174 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?175 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?176 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?177 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?178 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?179 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?180 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?181 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?182 | ?N | ?CH | ?CH | H | H | ?CH 3 | ?S(O) | O |
?183 | ?N | ?CH | ?CH | ?H | H | C 2H 5 | ?S(O) | O |
?184 | ?N | ?CH | ?CH | H | ?H | ?C 6H 5 | ?S(O) | O |
?185 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?186 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?187 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?188 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?189 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?190 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?191 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?192 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?193 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?S(O) | O |
?194 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?S(O) | O |
?195 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?S(O) | O |
?196 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?197 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?198 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?199 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?200 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?201 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?202 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?203 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?204 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?S(O) | O |
?205 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?S(O) | O |
?206 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ?S(O) | O |
?207 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?S(O) | O |
?208 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?S(O) | O |
?209 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?S(O) | O |
?210 | ?CH | ?CH | ?N | ?H | ?H | 2,3-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?211 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?212 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?213 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?S(O) | O |
?214 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?S(O) | O |
?215 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?SO 2 | O |
?216 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?SO 2 | O |
?217 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?SO 2 | O |
?218 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?SO 2 | O |
?219 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?SO 2 | O |
?220 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?SO 2 | O |
?221 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?222 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?223 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?224 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?225 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?SO 2 | ?O |
?226 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?CH 3 | ?SO 2 | ?O |
?227 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?C 2H 5 | ?SO 2 | ?O |
?228 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?C 6H 5 | ?SO 2 | ?O |
?229 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?230 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?231 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?232 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?233 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?234 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?235 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?236 | ?C | ?CH | ?CH | ?4-C 6H 5O | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?SO 2 | ?O |
?237 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?SO 2 | ?O |
?238 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?SO 2 | ?O |
?239 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?SO 2 | ?O |
?240 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?241 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?242 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?243 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?244 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?245 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?246 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?247 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?SO 2 | ?O |
?248 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?SO 2 | ?O |
?249 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?SO 2 | ?O |
?250 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?SO 2 | ?O |
?251 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?252 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?253 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?SO 2 | ?O |
?254 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?255 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?256 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?257 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O |
?258 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?SO 2 | ?O | ||
?259 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?SO 2 | ?O | ||
?260 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?SO 2 | ?O | ||
?261 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?SO 2 | ?O | ||
?262 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?263 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?264 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?265 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?266 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?267 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?268 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?269 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ?SO 2 | ?O | ||
?270 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?SO 2 | ?O | ||
?271 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?SO 2 | ?O | ||
?272 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?SO 2 | ?O | ||
?273 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?274 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?275 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?276 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?277 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?278 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?279 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?280 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?SO 2 | ?O | ||
?281 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?SO 2 | ?O | ||
?282 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?SO 2 | ?O | ||
?283 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?SO 2 | ?O | ||
?284 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?285 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?286 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?SO 2 | ?O | ||
?287 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?288 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?289 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?290 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?SO 2 | ?O | ||
?291 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?SO 2 | ?O | ||
?292 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?SO 2 | ?O | ||
?293 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?SO 2 | ?O | ||
?294 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?SO 2 | ?O |
?295 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?296 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?297 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?298 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?299 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?300 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?301 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?302 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ??SO 2 | ??O |
?303 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ??SO 2 | ??O |
?304 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ??SO 2 | ??O |
?305 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ??SO 2 | ??O |
?306 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?307 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?308 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?309 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?310 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?311 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?312 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?313 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ??SO 2 | ??O |
?314 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ??SO 2 | ??O |
?315 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ??SO 2 | ??O |
?316 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ??SO 2 | ??O |
?317 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?318 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?319 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??SO 2 | ??O |
?320 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?321 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?322 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?323 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2-C 6H 3 | ??SO 2 | ??O |
?324 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3-C 6H 2 | ??SO 2 | ??O |
Similarly, according to general technology E given below, might prepare according to following compounds of the present invention (embodiment 325 to 2634):
Embodiment 325-654:
A, C, D, R, R1, R6 and X have the as above given implication of embodiment 1-324, and Y is NH in each case;
Embodiment 655-984:
A, C, D, R, R1, R6 and X have the as above given implication of embodiment 1-324, and Y is N-CH in each case
3
Embodiment 985-1314:
A, C, D, R, R1, R6 and X have the as above given implication of embodiment 1-324, and Y is N-C in each case
2H
5
Embodiment 1315-1644:
A, C, D, R, R1, R6 and X have the as above given implication of embodiment 1-324, and Y is N-C in each case
6H
5
Embodiment 1645-1974:
A, C, D, R, R1, R6 and X have the as above given implication of embodiment 1-324, and Y is N-2-(CH in each case
3O)-C
6H
4
Embodiment 1975-2304:
A, C, D, R, R1, R6 and X have the as above given implication of embodiment 1-324, and Y is N-3-(CH in each case
3O)-C
6H
4
Embodiment 2305-2634:
A, C, D, R, R1, R6 and X have the as above given implication of embodiment 1-324, and Y is N-4-(CH in each case
3O)-C
6H
4
E) preparation is according to of the present invention 1,2, and the 4-triazine is the general technology of [4,5-a] indole derivatives also
Mono-substituted hydrazine derivative of 2 equivalents and glacial acetic acid (0.5ml/mmol) are joined in the propyl carbinol suspension (10ml/mmol) of 1 equivalent according to the 2-acyl indol of method A or B preparation, with mixture 16 hours (monitoring) of heating under refluxing with TLC.After being cooled to room temperature, pour reaction soln in the water (150ml/mmol), separate organic phase, water ethyl acetate extraction three times (10ml/mmol).Merge organic phase,, utilize rotatory evaporator to remove carefully and desolvate, crude product is dissolved in tetrahydrofuran (THF) (7.5ml/mmol) through dried over mgso.Add 1.3 equivalent N to this solution, N '-carbonyl dimidazoles adds 2.1 equivalent sodium hydrides (75% intensity white oil dispersion) then, after at room temperature 2 hours, mixture is heated 48 hours under refluxing.After being cooled to room temperature, pour reaction soln in the water (150ml/mmol), separate solid, product under atmospheric pressure pass through silica gel chromatography (mobile phase are an ether: hexane=1: 2).
Embodiment E 1 (D-70746):
Raw material A 5:(4-chloro-phenyl-)-(5-methoxyl group-1H-indoles-2-yl) ketone
Reagent E 1: phenylhydrazine
2-phenyl-6-(4-chloro-phenyl-)-1,2, the 4-triazine is [4,5-a] (5-methoxyl group indoles)-3-ketone also
M.p.:155-158℃
F) preparation is according to the general technology of pyrrolo-of the present invention [1,2-a] indole derivatives
1.1 equivalent solid hydride sodium (60-75% mineral oil dispersion) are joined the N of 1 equivalent according to the 2-acyl indol of method A or B preparation; among the N '-dimethyl formamide solution (10ml/mmol); each add a small amount of, at room temperature stir 5 minutes after, with mixture 90 ℃ of heating 1 hour down.Then room temperature is got back in the mixture cooling, drip the phenyl etheride that 1.1 equivalents suitably replace, mixture is heated 3 to 8 hours (monitoring with TLC) down at 90 ℃ once more.After being cooled to room temperature, pour reaction soln in the water (150ml/mmol), separate the precipitation that is generated, (mobile phase is an ether: hexane=1: 3) under atmospheric pressure to pass through silica gel chromatography.
Embodiment F 1 (D-80786):
Raw material A 5:(4-chloro-phenyl-)-(5-methoxyl group-1H-indoles-2-yl) ketone
M.p.:152-155 ℃ of 1-(4-chloro-phenyl-)-6-methoxyl group-2-phenyl-3a-azepine cyclopenta [a] indenes-3-ketone
Embodiment F 2 (D-80815):
Raw material B6:(5-methoxyl group-1H-indoles-2-yl)-(3-p-methoxy-phenyl) ketone
6-methoxyl group-1-(3-p-methoxy-phenyl)-2-phenyl-3a-azepine cyclopenta [a] indenes-3-ketone
M.p.:111-113℃
Embodiment F 3 (D-80816):
Raw material B6:(5-methoxyl group-1H-indoles-2-yl)-(3-p-methoxy-phenyl) ketone
6-methoxyl group-1, two (3-p-methoxy-phenyl)-3a-azepine cyclopenta [a] indenes of 2--3-ketone
M.p.:112-114℃
Embodiment F 4 (D-80819):
Raw material A 4:(5-methoxyl group-1H-indoles-2-yl)-(4-p-methoxy-phenyl) ketone
2-(4-fluorophenyl)-6-methoxyl group-1-(4-p-methoxy-phenyl)-3a-azepine cyclopenta [a] indenes-3-ketone
M.p.:157-160℃
Can prepare according to following compounds of the present invention (embodiment 2635 to 3842), from having the indole-2-carboxylic acid derivatives of different substituents according to above-mentioned synthesis technique F:
Raw material:
Product (n=0, Z=C-R8):
?No. | ??A | ?C | ?D | ?R | ?R1 | ?R6 | ?R8 | ?X |
?2635 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?CH 3 | ?C(O) |
?2636 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?C 2H 5 | ?C(O) |
?2637 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?C 6H 5 | ?C(O) |
?2638 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
?2639 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
?2640 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
?2641 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
?2642 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
?2643 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
?2644 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
?2645 | ?CH | ?CH | ?CH | ?H | ?H | ?CH 3 | 3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
?2646 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?CH 3 | ?C(O) |
?2647 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?C 2H 5 | ?C(O) |
?2648 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?C 6H 5 | ?C(O) |
?2649 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
?2650 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
?2651 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
?2652 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
?2653 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
?2654 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
?2655 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
?2656 | ?CH | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
?2657 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?CH 3 | ?C(O) |
?2658 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) |
?2659 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) |
?2660 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
?2661 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
?2662 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
?2663 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
?2664 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
?2665 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
?2666 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
?2667 | ?CH | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
?2668 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
?2669 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2670 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
2671 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2672 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2673 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2674 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2675 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2676 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2677 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2678 | ?CH | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2679 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
2680 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2681 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
2682 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2683 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2684 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2685 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2686 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2687 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2688 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2689 | ?CH | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2690 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
2691 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2692 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
2693 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2694 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2695 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2696 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2697 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2698 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2699 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2700 | ?CH | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2701 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2702 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2703 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2704 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2705 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2706 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2707 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2708 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2709 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2710 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2711 | ?CH | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2712 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2713 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2714 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2715 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2716 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2717 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2718 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2719 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2720 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2721 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2722 | ?CH | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2723 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2724 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2725 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2726 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2727 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2728 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2729 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2730 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2731 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2732 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2733 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2734 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2735 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2736 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2737 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2738 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2739 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2740 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2741 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2742 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2743 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2744 | ?CH | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2745 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
2746 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
2747 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
2748 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2749 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2750 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2751 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2752 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2753 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2754 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2755 | ?CH | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2756 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?CH 3 | ?C(O) |
2757 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?C 2H 5 | ?C(O) |
2758 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?C 6H 5 | ?C(O) |
2759 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2760 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2761 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2762 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2763 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2764 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2765 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2766 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2767 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?CH 3 | ?C(O) |
2768 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?C 2H 5 | ?C(O) |
2769 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?C 6H 5 | ?C(O) |
2770 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2771 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2772 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2773 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2774 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2775 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2776 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2777 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2778 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?CH 3 | ?C(O) |
2779 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) |
2780 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) |
2781 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2782 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2783 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2784 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2785 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2786 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2787 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2788 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2789 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
2790 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2791 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
2792 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2793 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2794 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2795 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2796 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2797 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2798 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2799 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2800 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
2801 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2802 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
2803 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2804 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2805 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2806 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2807 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2808 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2809 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2810 | ?C | ?CH | ?CH | 4-C 6H 5O | H | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2811 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
2812 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2813 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
2814 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2815 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2816 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2817 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2818 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2819 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2820 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2821 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2822 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2823 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2824 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2825 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2826 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2827 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2828 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2829 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2830 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2831 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2832 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2833 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2834 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2835 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2836 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2837 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2838 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2839 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2840 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2841 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2842 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2843 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2844 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2845 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2846 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2847 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2848 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2849 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2850 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2851 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2852 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2853 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2854 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2855 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2856 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2857 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2858 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2859 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2860 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2861 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2862 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2863 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2864 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2865 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2866 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
2867 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
2868 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
2869 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2870 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2871 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2872 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2873 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2874 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2875 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2876 | ?C | ?CH | ?CH | ?4- C 6H 5O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2877 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?CH 3 | ?C(O) |
2878 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?C 2H 5 | ?C(O) |
2879 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?C 6H 5 | ?C(O) |
2880 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2881 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2882 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2883 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2884 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2885 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2886 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2887 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2888 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?CH 3 | ?C(O) |
2889 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?C 2H 5 | ?C(O) |
2890 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?C 6H 5 | ?C(O) |
2891 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2892 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2893 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2894 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2895 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2896 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2897 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2898 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2899 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?CH 3 | ?C(O) |
2900 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) |
2901 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) |
2902 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2903 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2904 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2905 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2906 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2907 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2908 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2909 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2910 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
2911 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2912 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
2913 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2914 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2915 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2916 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2917 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2918 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2919 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2920 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2921 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
2922 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2923 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2924 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2925 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2926 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2927 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2928 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2929 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2930 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
2931 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
2932 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
2933 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2934 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2935 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2936 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | 2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2937 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | 2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2938 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2939 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2940 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2941 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2942 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2943 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2944 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2945 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2946 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2947 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2948 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2949 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2950 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2951 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2952 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2953 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2954 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2955 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2956 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2957 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2958 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2959 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2960 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2961 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2962 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2963 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2964 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2965 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2966 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2967 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2968 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2969 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2970 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2971 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2972 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2973 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2974 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
2975 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
2976 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
2977 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2978 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2979 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2980 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2981 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2982 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2983 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2984 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2985 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
2986 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
2987 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
2988 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
2989 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
2990 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
2991 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
2992 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2993 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
2994 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
2995 | ?CH | ?CH | ?CH | ?5-CH 3O | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
2996 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?CH 3 | ?C(O) |
2997 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?C 2H 5 | ?C(O) |
2998 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?C 6H 5 | ?C(O) |
2999 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3000 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3001 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3002 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3003 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3004 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3005 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3006 | ?CH | ?C | ?CH | ?6-F | ?H | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3007 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?CH 3 | ?C(O) |
3008 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?C 2H 5 | ?C(O) |
3009 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?C 6H 5 | ?C(O) |
3010 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3011 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3012 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3013 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3014 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3015 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3016 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3017 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3018 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?CH 3 | ?C(O) |
3019 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) |
3020 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) |
3021 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3022 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3023 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3024 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3025 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3026 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3027 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3028 | ?CH | ?C | ?CH | ?6-F | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3029 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3030 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3031 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3032 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3033 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3034 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3035 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3036 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3037 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3038 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3039 | ?CH | ?C | ?CH | ?6-F | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3040 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3041 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3042 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3043 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3044 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3045 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3046 | ?CH | ?C | ?CH | ?6-F | ?H | 3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3047 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3048 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3049 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3050 | ?CH | ?C | ?CH | ?6-F | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3051 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3052 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3053 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3054 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3055 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3056 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3057 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3058 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3059 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3060 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3061 | ?CH | ?C | ?CH | ?6-F | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3062 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3063 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3064 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3065 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3066 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3067 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3068 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3069 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3070 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3071 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3072 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3073 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3074 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3075 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3076 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3077 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3078 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3079 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3080 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3081 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3082 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3083 | ?CH | ?C | ?CH | ?6-F | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3084 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3085 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3086 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3087 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3088 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3089 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3090 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3091 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3092 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3093 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3094 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3095 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3096 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3097 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3098 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3099 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3100 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3101 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3102 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3103 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3104 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3105 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3106 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
3107 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
3108 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
3109 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3110 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3111 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3112 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3113 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3114 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3115 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3116 | ?CH | ?C | ?CH | ?6-F | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3117 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?CH 3 | ?C(O) |
3118 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?C 2H 5 | ?C(O) |
3119 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?C 6H 5 | ?C(O) |
3120 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3121 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3122 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3123 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3124 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3125 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3126 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3127 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3128 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?CH 3 | ?C(O) |
3129 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?C 2H 5 | ?C(O) |
3130 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?C 6H 5 | ?C(O) |
3131 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3132 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3133 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3134 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3135 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3136 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3137 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3138 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3139 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?CH 3 | ?C(O) |
3140 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) |
3141 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) |
3142 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3143 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3144 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3145 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3146 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3147 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3148 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3149 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3150 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3151 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3152 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3153 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3154 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3155 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3156 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3157 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3158 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3159 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3160 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3161 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3162 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3163 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3164 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3165 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3166 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3167 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3168 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3169 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3170 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3171 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3172 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3173 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3174 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3175 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3176 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3177 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3178 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3179 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3180 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3181 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3182 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3183 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3184 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3185 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3186 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3187 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3188 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3189 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3190 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3191 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3192 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3193 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3194 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3195 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3196 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3197 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3198 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3199 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3200 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3201 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3202 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3203 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3204 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3205 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3206 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3207 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3208 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3209 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3210 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3211 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3212 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3213 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3214 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3215 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3216 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3217 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3218 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3219 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3220 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3221 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3222 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3223 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3224 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3225 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3226 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3227 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
3228 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
3229 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
3230 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3231 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3232 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3233 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3234 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3235 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3236 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3237 | ?CH | ?CH | ?C | ?7-CH 3 | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3238 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?CH 3 | ?C(O) |
3239 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?C 2H 5 | ?C(O) |
3240 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?C 6H 5 | ?C(O) |
3241 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3242 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3243 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3244 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3245 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3246 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3247 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3248 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3249 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?CH 3 | ?C(O) |
3250 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?C 2H 5 | ?C(O) |
3251 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?C 6H 5 | ?C(O) |
3252 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3253 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3254 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3255 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3256 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3257 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3258 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3259 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3260 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?CH 3 | ?C(O) |
3261 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?C 2H 5 | ?C(O) |
3262 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?C 6H 5 | ?C(O) |
3263 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3264 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3265 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3266 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3267 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3268 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3269 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3270 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3271 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3272 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3273 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3274 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3275 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3276 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3277 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3278 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3279 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3280 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3281 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3282 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3283 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3284 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3285 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3286 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3287 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3288 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3289 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3290 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3291 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3292 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3293 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3294 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3295 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3296 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3297 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3298 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3299 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3300 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3301 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3302 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3303 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3304 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3305 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3306 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3307 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | 2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3308 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3309 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3310 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3311 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3312 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3313 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3314 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3315 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3316 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3317 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3318 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3319 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3320 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3321 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3322 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3323 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3324 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3325 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3326 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3327 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3328 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3329 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3330 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3331 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3332 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3333 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3334 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3335 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3336 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3337 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3338 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3339 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3340 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3341 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3342 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3343 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3344 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3345 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3346 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3347 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3348 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
3349 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
3350 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
3351 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3352 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3353 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3354 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3355 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3356 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3357 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3358 | ?CH | ?CH | ?CH | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3359 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?CH 3 | ?C(O) |
3360 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?C 2H 5 | ?C(O) |
3361 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?C 6H 5 | ?C(O) |
3362 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3363 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3364 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3365 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3366 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3367 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3368 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3369 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3370 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?CH 3 | ?C(O) |
3371 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?C 2H 5 | ?C(O) |
3372 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?C 6H 5 | ?C(O) |
3373 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3374 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3375 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3376 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3377 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3378 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3379 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3380 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3381 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?CH 3 | ?C(O) |
3382 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?C 2H 5 | ?C(O) |
3383 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?C 6H 5 | ?C(O) |
3384 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3385 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3386 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3387 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3388 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3389 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3390 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3391 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3392 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3393 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3394 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3395 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3396 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3397 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3398 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3399 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3400 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3401 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3402 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3403 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3404 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3405 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3406 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3407 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3408 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3409 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3410 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3411 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3412 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3413 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3414 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3415 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3416 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3417 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3418 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3419 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3420 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3421 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3422 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3423 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3424 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3425 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3426 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3427 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3428 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3429 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3430 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3431 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3432 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3433 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3434 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3435 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3436 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3437 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3438 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3439 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3440 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3441 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3442 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3443 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3444 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3445 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3446 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3447 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3448 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3449 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3450 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3451 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3452 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3453 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3454 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3455 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3456 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3457 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3458 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3459 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3460 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3461 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3462 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3463 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3464 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3465 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3466 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3467 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3468 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3469 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
3470 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
3471 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
3472 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3473 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3474 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3475 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3476 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3477 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3478 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3479 | ?CH | ?CH | ?CH | ?5-Cl | ?C 6H 5 | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3480 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?CH 3 | ?C(O) |
3481 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?C 2H 5 | ?C(O) |
3482 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?C 6H 5 | ?C(O) |
3483 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3484 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3485 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3486 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3487 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3488 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3489 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3490 | ?N | ?CH | ?CH | ?H | ?H | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3491 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?CH 3 | ?C(O) |
3492 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?C 2H 5 | ?C(O) |
3493 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?C 6H 5 | ?C(O) |
3494 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3495 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3496 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3497 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3498 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3499 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3500 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3501 | ?N | ?CH | ?CH | ?H | ?H | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3502 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?CH 3 | ?C(O) |
3503 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) |
3504 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) |
3505 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3506 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3507 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3508 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3509 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3510 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3511 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3512 | ?N | ?CH | ?CH | ?H | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3513 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3514 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3515 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3516 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3517 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3518 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3519 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3520 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3521 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3522 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3523 | ?N | ?CH | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3524 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3525 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3526 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3527 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3528 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3529 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3530 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3531 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3532 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3533 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3534 | ?N | ?CH | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3535 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3536 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3537 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3538 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3539 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3540 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3541 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3542 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3543 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3544 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3545 | ?N | ?CH | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3546 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3547 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3548 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3549 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3550 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3551 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3552 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3553 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3554 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3555 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3556 | ?N | ?CH | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3557 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3558 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3559 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3560 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3561 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3562 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3563 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3564 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3565 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3566 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3567 | ?N | ?CH | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3568 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3569 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3570 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3571 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3572 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3573 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3574 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3575 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3576 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3577 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3578 | ?N | ?CH | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3579 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3580 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3581 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3582 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3583 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3584 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3585 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3586 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3587 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3588 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3589 | ?N | ?CH | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3590 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
3591 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
3592 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
3593 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3594 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3595 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3596 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3597 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3598 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3599 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3600 | ?N | ?CH | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3601 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?CH 3 | ?C(O) |
3602 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?C 2H 5 | ?C(O) |
3603 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?C 6H 5 | ?C(O) |
3604 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3605 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3606 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3607 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3608 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3609 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3610 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3611 | ?CH | ?N | ?CH | ?H | ?H | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3612 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?CH 3 | ?C(O) |
3613 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?C 2H 5 | ?C(O) |
3614 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?C 6H 5 | ?C(O) |
3615 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3616 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3617 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3618 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3619 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3620 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3621 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3622 | ?CH | ?N | ?CH | ?H | ?H | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3623 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?CH 3 | ?C(O) |
3624 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) |
3625 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) |
3626 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3636 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3628 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3629 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3630 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3631 | ?CH | N | ?CH | ?H | ?H | ?C 6H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3632 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3633 | ?CH | ?N | ?CH | ?H | ?H | ?C 6H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3634 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3635 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3636 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3637 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3638 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3639 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3640 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3641 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3642 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3643 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3644 | ?CH | ?N | ?CH | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3645 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3646 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3647 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3648 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3649 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3650 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3651 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3652 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3653 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3654 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3655 | ?CH | ?N | ?CH | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3656 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?CH 3 | ?C(O) |
3657 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C 2H 5 | ?C(O) |
3658 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?C 6H 5 | ?C(O) |
3659 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3660 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3661 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3662 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3663 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3664 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3665 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3666 | ?CH | ?N | ?CH | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3667 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3668 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3669 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3670 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3671 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3672 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3673 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3674 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3675 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3676 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3677 | ?CH | ?N | ?CH | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3678 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3679 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3680 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3681 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3682 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3683 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3684 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3685 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3686 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3687 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3688 | ?CH | ?N | ?CH | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3689 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3690 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3691 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3692 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3693 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3694 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3695 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3696 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3697 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3698 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3699 | ?CH | ?N | ?CH | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3700 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3701 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3702 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3703 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3704 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3705 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3706 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3707 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3708 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3709 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3710 | ?CH | ?N | ?CH | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3711 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
3712 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
3713 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
3714 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3715 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3716 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3717 | ?CH | ?N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3718 | ?CH | ??N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3719 | ?CH | ??N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3720 | ?CH | ??N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3721 | ?CH | ??N | ?CH | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3722 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?CH 3 | ?C(O) |
3723 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?C 2H 5 | ?C(O) |
3724 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?C 6H 5 | ?C(O) |
3725 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3726 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3727 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3728 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3729 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3730 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3731 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3732 | ?CH | ?CH | ?N | ?H | ?H | ?CH 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3733 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?CH 3 | ?C(O) |
3734 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?C 2H 5 | ?C(O) |
3735 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?C 6H 5 | ?C(O) |
3736 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3737 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3738 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3739 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3740 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3741 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3742 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3743 | ?CH | ?CH | ?N | ?H | ?H | ?C 2H 5 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3744 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ?CH 3 | ?C(O) |
3745 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ?C 2H 5 | ?C(O) |
3746 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ?C 6H 5 | ?C(O) |
3747 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3748 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3749 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3750 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ??2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3751 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ??2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3752 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ??3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3753 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ??3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3754 | ?CH | ?CH | ?N | ?H | ?H | ?C 6H 5 | ??3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3755 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??CH 3 | ?C(O) |
3756 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??C 2H 5 | ?C(O) |
3757 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??C 6H 5 | ?C(O) |
3758 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??2-(CH 3O)-C 6H 4 | ?C(O) |
3759 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??3-(CH 3O)-C 6H 4 | ?C(O) |
3760 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??4-(CH 3O)-C 6H 4 | ?C(O) |
3761 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3762 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3763 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3764 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3765 | ?CH | ?CH | ?N | ?H | ?H | ?2-(CH 3O)-C 6H 4 | ??3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3766 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??CH 3 | ?C(O) |
3767 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??C 2H 5 | ?C(O) |
3768 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??C 6H 5 | ?C(O) |
3769 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??2-(CH 3O)-C 6H 4 | ?C(O) |
3770 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??3-(CH 3O)-C 6H 4 | ?C(O) |
3771 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??4-(CH 3O)-C 6H 4 | ?C(O) |
3772 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3773 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3774 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3775 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3776 | ?CH | ?CH | ?N | ?H | ?H | ?3-(CH 3O)-C 6H 4 | ??3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3777 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??CH 3 | ?C(O) |
3778 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??C 2H 5 | ?C(O) |
3779 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??C 6H 5 | ?C(O) |
3780 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??2-(CH 3O)-C 6H 4 | ?C(O) |
3781 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??3-(CH 3O)-C 6H 4 | ?C(O) |
3782 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??4-(CH 3O)-C 6H 4 | ?C(O) |
3783 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3784 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3785 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ??3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3786 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3787 | ?CH | ?CH | ?N | ?H | ?H | ?4-(CH 3O)-C 6H 4 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3788 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3789 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3790 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3791 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3792 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3793 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3794 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3795 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3796 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3797 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3798 | ?CH | ?CH | ?N | ?H | ?H | ?2,3-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3799 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3800 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3801 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3802 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3803 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3804 | ?CH | ??CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3805 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3806 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3807 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3808 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3809 | ?CH | ?CH | ?N | ?H | ?H | ?2,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3810 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3811 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3812 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3813 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3814 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3815 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3816 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3817 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3818 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3819 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3820 | ?CH | ?CH | ?N | ?H | ?H | ?3,4-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3821 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?CH 3 | ?C(O) |
3822 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 2H 5 | ?C(O) |
3823 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?C 6H 5 | ?C(O) |
3824 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3825 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3-(CH 3O)-C 6H 4 | ?C(O) |
3826 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?4-(CH 3O)-C 6H 4 | ?C(O) |
3827 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3828 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3829 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3830 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3831 | ?CH | ?CH | ?N | ?H | ?H | ?3,5-(CH 3O) 2- C 6H 3 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
3832 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?CH 3 | ?C(O) |
3833 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 2H 5 | ?C(O) |
3834 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?C 6H 5 | ?C(O) |
3835 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2-(CH 3O)-C 6H 4 | ?C(O) |
3836 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3-(CH 3O)-C 6H 4 | C(O) |
3837 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?4-(CH 3O)-C 6H 4 | C(O) |
3838 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,3-(CH 3O) 2-C 6H 3 | ?C(O) |
3839 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?2,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3840 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4-(CH 3O) 2-C 6H 3 | ?C(O) |
3841 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,5-(CH 3O) 2-C 6H 3 | ?C(O) |
3842 | ?CH | ?CH | ?N | ?H | ?H | ?3,4,5-(CH 3O) 3- C 6H 2 | ?3,4,5-(CH 3O) 3-C 6H 2 | ?C(O) |
Similarly, according to general technology F, also might prepare according to following compounds of the present invention (embodiment 3843 to 6260):
Embodiment 3843-5051:
A, C, D, R, R1, R6, R8 and X have the given implication of as above embodiment 2635 to 3842, and Y is S (O) in each case;
Embodiment 5052-6260:
A, C, D, R, R1, R6, R8 and X have the given implication of as above embodiment 2635 to 3842, and Y is SO in each case
2
Pharmacological tests
The in vitro tests of being carried out in selected tumor model shows following pharmacologically active.
Embodiment 1: anti proliferative properties
Use set tumor cell line, in proliferation assay, check antiproliferative activity (the Scudiero et al. of material D-70260, D-70744, D-80815, D-80816 and D-80819 (Embodiment C 2.3, D4, F2, F3 and F4), Cancer Res., 48:4827-33,1987).Used test determination the mitochondrial dehydrogenase activity, allow cell survival, indirect measurement cell count.Used clone is human cell line HeLa/KB (CCL17), SK-OV-3 (HTB77), MCF-7 (HTB22) and murine leukemia clone L1210 (CCL219).They have been differentiated very fully, obtain set clone from ATCC, cultivate it.
The result that table 1 is summed up shows that material D-70260, D-70744 and D-80816 (Embodiment C 2.3, D4 and F3) have very strong antiproliferative effect.On the contrary, relevant Compound D-80815 and D-80819 (embodiment F 2 and F4) shows not significant effect on the structure.Therefore, there is clear and definite structure-activity relation.
Table 1: different derivatives pair cell in the XTT cell toxicity test is the antiproliferative activity of HeLa/KB, SK-OV-3, MCF-7 and L1210.The restraining effect that is noted that represent with the per-cent under 3.16 μ g/ml concentration.
Fig. 1: D-80816 (embodiment F 3) pair cell in the XTT cell toxicity test is the concentration dependent antiproliferative activity diagram (A) of HeLa/KB, SK-OV-3, MCF-7 and L1210.
D-80816
Embodiment 2:D-80816 (embodiment F 3) is the effect in the tubular fibre model in vivo
In order to be determined at utilizability and the effect in the animal model (nude mice), culturing cell is HeLa/KB, MCF-7 and L1210 (Hollingshead el al., Life Sciences 57,131-41,1995) in the tubular fibre of i.p. or s.c. implantation.To be administered four times for examination material D-80816, dosage is 100mg/kg i.p..After treatment in the 5th day finishes, transplant out fiber, utilize the XTT assay method to measure the cell viability of gained tumour cell.D-80816 shows that to all cells system and implant site maximum 100% suppresses general toxicity LD
50>1000mg/kg (i.p.).
Show 2:D-80816 activity in vivo (dosage: 4 * 100mg/kg i.p.) to tumor cell line HeLa/KB, MCF-7 and L1210 in the tubular fibre test
The cell cycle specific effect of embodiment 3:D-80816 in the RKOp27 model
Use RKOp27 cell system (M.Schmidt et al., Oncogene 19 (20): 2423-9,2000) as model, check the cell cycle specific effect.RKO is human colon carcinoma system, wherein ecdysone expression system abduction delivering cell cycle inhibitor p27
Kip1, stop at G1 (Fig. 2) with causing cell cycle specific.Material with nonspecific action suppresses propagation, whether stops at G1 with the RKO cell and has nothing to do.On the contrary, cell cycle specific material, for example Antitubulin only have cytotoxicity when cell does not stop and experiencing the cell cycle.Here, the effect of D-80816 showed cell period specific that is to say, only do not stop at cell cycle G1 not by inducing cell in just can measure concentration dependent antiproliferative effect (Fig. 3).Therefore, have to suppose that D-80816 and derivative act as certain clear and definite molecule mechanism.
Fig. 2: induce p27/kip1 to express to cause the cell cycle stop at the diagram of G1 and cell+/-inductor (muristerone A) and diagram for the processing sequence of examination material
Fig. 3: D-80816 (embodiment F 3) to stop at the cell cycle G1 phase (derivative) or experiencing the cell cycle, be the anti-proliferative effect of the RKO colon cancer cell of exponential growth
The explanation of method therefor
The active XTT test of cell deoxygenase
At 37 ℃, 5%CO
2Under 95% atmospheric moisture, in stifling thermostat container, under standard conditions, cultivate and adhere to growing tumors clone HeLa/KB, SK-OV-3, MCF-7, L1210.At the 1st day of experiment, use trypsinase/EDTA to peel off cell, centrifugation.Subsequently, cell precipitation is suspended in separately the substratum again by suitable cell count, in 96 hole microtiter plates, reacts.Then with flat board overnight incubation in stifling thermostat container.Preparation was diluted to suitable concentration at the 2nd day that tests with substratum for the 10mM stock solution of examination material in DMSO.Add the substratum that contains material to cell then, in stifling thermostat container, cultivated 45 hours.In contrast, use the cell for the examination mass treatment of no use.With regard to the XTT assay method, 1mg/ml XTT (3 '-[1-(phenylamino carbonyl)-3,4-tetrazolium] two (4-methoxyl group-6-nitro) benzene sulfonic acid sodium salt) is dissolved in do not contain in the phenol red RPMI-1640 substratum.In addition, the solution of preparation 0.383mg/ml PMS (N-methyldiphenyl and pyrazine Methylsulfate) in phosphoric acid buffers saline solution (PBS).At the 4th day of experiment, on the cell flat board, move and add 75 μ l/ hole XTT-PMS mixtures, cultivated 45 hours during this period with for the examination material.For this reason, before use with XTT solution and PMS solution by 50: 1 (v: v) mix.Then the cell flat board was cultivated other 3 hours in stifling thermostat container, in photometer, measured optical density(OD) (OD
490nm).
By the OD that is measured
490nm, calculate inhibition per-cent with respect to contrast, draw concentration-activity curve in the semilog mode.Utilize the Graphpad program to calculate IC by regression analysis from concentration-activity curve
50
The mensuration of antiproliferative activity in the tubular fibre model in the body
The tubular fibre that Xiang Youju (vinylidene) fluorine is made is introduced tumor cell line HeLa/KB, MCF-7 and L1210 (5 * 10
6Cell/ml), be transplanted to the physiology body cavity interior (intraperitoneal i.p. or subcutaneous s.c.) of nude mice.Supply in the examination animal at every, (3i.p. 3s.c.), wherein contains relevant tumor cell line to total 6 tubular fibres of co-transplantation.(can with one group of 6 animal with supplying to try mass treatment (every day, 1 i.p. amounted to 4 days)?).Only use the animal served as control group of solvent tylose processing.Last application of substances is transplanted out tubular fibre one day after.Utilize the XTT assay method to measure in every tubular fibre metabolic activity, great-hearted cell count (on seeing) are arranged.Measure anti-tumor activity thus, represent with inhibition % with respect to contrast for the examination material.
Utilize the cell cycle analysis of RKOp27 model
This assay method is carried out in 96 hole flat boards.Derivable p27
Kip1Expression stops the growth of cell fully, but cell does not have death.To being induced and the effect of derivative cell not, might draw conclusion by relatively about the therapeutical agent mechanism of action (cell cycle specific).Inoculate not derivative cell, compare high about four times of cell count with not derivative cell, (derivative cell is 2 * 10 because no longer break up between test period
4Individual/hole, not derivative cell is 0.6 * 10
4Individual/hole).Contrast is not processed cell (+/-induce).Induce with 3 μ M muristerone A and carry out.The 1st day, inoculating cell (+/-muristeroneA), cultivated 24 hours down at 37 ℃.The 2nd day, add for examination material (contrast is DMSO), sample was cultivated other 48 hours down at 37 ℃, carry out standard x TT then and measure (on seeing).
Can be used as pharmacological agent Mammals, particularly Human diseases, particularly tumor disease according to compound of the present invention.
Can be oral, part or parenteral mode (i.m., i.v., s.c.) form of administration administration to be fit to.
The example of the form of administration that is fit to that can mention has:
Example I
The tablet that comprises the 50mg active compound
Form:
(1) active compound 50.0mg
(2) lactose 98.0mg
(3) W-Gum 50.0mg
(4) polyvinylpyrrolidone 15.0mg
(5) Magnesium Stearate 2.0mg
Amount to: 215.0mg
Preparation:
(1), (2) and (3) are mixed, use the aqueous solution granulation of (4).(5) are mixed with dry granules.With this mixture compacting in flakes.
Example II
The capsule that comprises the 50mg active compound
Form:
(1) active compound 50.0mg
(2) exsiccant W-Gum 58.0mg
(3) pulverous lactose 50.0mg
(4) Magnesium Stearate 2.0mg
Amount to: 160.0mg
Preparation:
(1) and (3) are ground.At violent blended simultaneously, this mixture is joined in the mixture of (2) and (4).In capsule filling machine, this powdered mixture is filled in No. 3 hard gelatin capsules.
Claims (7)
1, formula I compound or its tautomer, steric isomer, mixture or pharmacy acceptable salt
Wherein
R1 is a hydrogen, (C6-C14)-aryl-unsubstituted or replaced wholly or in part by identical or different substituting group, (C1-C13)-and heteroaryl-contain at least one to four N, NH, O and/or S are as ring members and be unsubstituted or replaced wholly or in part by identical or different substituting group, (C3-C8)-cycloalkyl-unsubstituted or replaced wholly or in part by identical or different substituting group, perhaps straight or branched (C1-C20)-alkyl-unsubstituted or replaced wholly or in part by identical or different substituting group;
A, B, C or D be nitrogen-atoms or the carbon atom for being replaced by R2-R5 independently of one another;
R2, R3, R4 and R5 are free electron to (if the bonding companion is A independently of one another, B, C or D are nitrogen-atoms), hydrogen, halogen, cyano group, nitro, hydroxyl, straight or branched (C1-C6)-alkyl, straight or branched (the C1-C6)-alkyl that is replaced by one or more halogen atoms, straight or branched (C1-C6)-alkoxyl group, straight or branched (the C1-C6)-alkoxyl group that is replaced by one or more halogen atoms, straight or branched (C1-C6)-alkylene dioxo base, (C1-C6)-the alkyl-carbonyl oxygen base, (C1-C6)-alkoxy-carbonyl oxy, (C1-C6)-alkylthio, (C1-C6)-alkyl sulphinyl, (C1-C6)-alkyl sulphonyl, carboxyl, (C1-C6)-alkyl carboxylic acid ester, acid amides, N-(C1-C6)-alkylamide, N, N-two-(C1-C6)-alkylamide, (C1-C6)-alkoxyl group-(C1-C6)-alkyl, amino, single-(C1-C6)-alkylamino, two-(C1-C6)-alkylamino-wherein two (C1-C6) groups can constitute optional one or more NH that contain together, N-(C1-C6)-alkyl, the ring of O or S, (C6-C14)-aryl, (C6-C14)-aryloxy, (C6-C14)-aryl-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C6)-alkoxyl group-(C1-C6)-alkyl, (C1-C6)-alkyl-carbonyl, (C1-C6)-alkoxy carbonyl, hydroxyl, wherein the group of two direct neighbors can be connected to each other;
R6 is (C6-C14)-aryl-unsubstituted or is replaced wholly or in part by identical or different substituting group, (C1-C13)-and heteroaryl-at least one is arranged to four N, NH, O and/or S are as ring members and be unsubstituted or replaced wholly or in part by identical or different substituting group, (C3-C8)-cycloalkyl-unsubstituted or replaced wholly or in part by identical or different substituting group, straight or branched (C1-C20)-alkyl-unsubstituted or replaced wholly or in part by identical or different substituting group, wherein identical or different substituting group is selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, hydroxyl, (C1-C6)-alkyl, (C1-C6)-alkoxyl group, carboxyl, (the C1-C6)-alkyl that is replaced by one or more identical or different halogen atoms, (the C1-C6)-alkoxyl group that is replaced by one or more identical or different halogen atoms, straight or branched (C2-C6)-thiazolinyl, straight or branched (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, straight or branched (C1-C6)-alkoxyl group, straight or branched (C1-C6)-alkylene dioxo base, (C1-C6)-alkoxyl group-(C1-C6)-alkyl, (C6-C14)-aryl, (C6-C14)-aryl-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C4)-alkoxyl group-(C1-C6)-alkyl;
X is carbonyl (C=O), sulfoxide (S=O) or alkylsulfonyl (SO
2);
Y is Sauerstoffatom or the nitrogen-atoms (NR7) that replaced by radicals R 7, wherein
R7 is (C6-C14)-aryl-unsubstituted or is replaced wholly or in part by identical or different substituting group, (C1-C13)-and heteroaryl-contain at least one to four N, NH, O and/or S are as ring members and be unsubstituted or replaced wholly or in part by identical or different substituting group, (C3-C8)-cycloalkyl-unsubstituted or replaced wholly or in part by identical or different substituting group, straight or branched (C1-C20)-alkyl-unsubstituted or replaced wholly or in part by identical or different substituting group, wherein identical or different substituting group is selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, hydroxyl, (C1-C6)-alkyl, (C1-C6)-alkoxyl group, carboxyl, (the C1-C6)-alkyl that is replaced by one or more identical or different halogen atoms, (the C1-C6)-alkoxyl group that is replaced by one or more identical or different halogen atoms, straight or branched (C2-C6)-thiazolinyl, straight or branched (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, straight or branched (C1-C6)-alkoxyl group, straight or branched (C1-C6)-alkylene dioxo base, (C1-C6)-alkoxyl group-(C1-C6)-alkyl, the straight or branched list-(C1-C6)-alkylamino, straight or branched two-(C1-C6)-alkylamino-wherein two (C1-C4) groups can constitute optional one or more NH that contain together, N-(C1-C6)-alkyl, the ring of O or S, (C6-C14)-aryl, (C6-C14)-aryl-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C4)-alkoxyl group-(C1-C6)-alkyl, (C1-C6)-alkyl-carbonyl, (C1-C6)-alkoxy carbonyl;
N is 0 or 1, and its condition is if n=0, so
The carbon atom that Z is replaced by radicals R 8 (C-R8), wherein
R8 is (C6-C14)-aryl-unsubstituted or is replaced wholly or in part by identical or different substituting group, (C1-C13)-and heteroaryl-contain at least one to four N, NH, O and/or S are as ring members and be unsubstituted or replaced wholly or in part by identical or different substituting group, (C3-C8)-cycloalkyl-unsubstituted or replaced wholly or in part by identical or different substituting group, straight or branched (C1-C20)-alkyl-unsubstituted or replaced wholly or in part by identical or different substituting group, wherein identical or different substituting group is selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, hydroxyl, (C1-C6)-alkyl, (C1-C6)-alkoxyl group, carboxyl, (the C1-C6)-alkyl that is replaced by one or more identical or different halogen atoms, (the C1-C6)-alkoxyl group that is replaced by one or more identical or different halogen atoms, straight or branched (C2-C6)-thiazolinyl, straight or branched (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, straight or branched (C1-C6)-alkoxyl group, straight or branched (C1-C6)-alkylene dioxo base, straight or branched (C1-C6)-alkylthio, (C1-C4)-alkyl sulphinyl, (C1-C4)-alkyl sulphonyl, (C6-C14)-arylthio, (C6-C14)-aryl sulfonyl kia, (C6-C14)-aryl sulfonyl, (C1-C6)-alkoxyl group-(C1-C6)-alkyl, the straight or branched list-(C1-C6)-alkylamino, straight or branched two-(C1-C6)-alkylamino-wherein two (C1-C4) groups can constitute optional one or more NH that contain together, N-(C1-C6)-alkyl, the ring of O or S, (C6-C14)-aryl, (C6-C14)-aryloxy, (C6-C14)-aryl-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C4)-alkoxyl group-(C1-C6)-alkyl, (C1-C6)-alkyl-carbonyl, (C1-C6)-alkoxy carbonyl, straight or branched list-N-(C1-C6)-alkyl-carbonyl-amino, straight or branched two-N, N-(C1-C6)-alkyl-carbonyl-amino, straight or branched list-N-(C1-C6)-alkoxycarbonyl amino, straight or branched two-N, N-(C1-C6)-alkoxycarbonyl amino, straight or branched N-(C1-C6)-alkyl-carbonyl-amino-N-(C1-C6)-alkylamino, straight or branched N-(C1-C6)-alkoxycarbonyl amino-N-(C1-C6)-alkylamino;
And if n=1, so
Z is a nitrogen-atoms.
2; as claim 1 claimed compounds; it is characterized in that R1 is a hydrogen; R2; R3; R4 and R5 are hydrogen independently of one another; halogen or (C1-C6)-alkoxyl group; R6 is straight or branched (C1-C20)-alkyl-unsubstituted or is replaced wholly or in part by identical or different substituting group; or (C6-C14)-aryl-unsubstituted or replaced wholly or in part by identical or different substituting group; its substituting group is selected from (C1-C6)-alkoxyl group and halogen; Y is Sauerstoffatom or group N-R7; wherein R7 is (C6-C14)-aryl-unsubstituted or is replaced wholly or in part by identical or different substituting group; X is carbonyl (C=O), and Z is nitrogen-atoms and n=1.
3; as claim 1 claimed compounds; it is characterized in that R1 is a hydrogen; R2; R3; R4 and R5 are hydrogen independently of one another; halogen or (C1-C6)-alkoxyl group; R6 is straight or branched (C1-C20)-alkyl-unsubstituted or is replaced wholly or in part by identical or different substituting group; or (C6-C14)-aryl-unsubstituted or replaced wholly or in part by identical or different substituting group; its substituting group is selected from (C1-C6)-alkoxyl group and halogen; n=0; Z is group C-R8; wherein R8 is (C6-C14)-aryl-unsubstituted or is replaced wholly or in part by identical or different substituting group, and it is carbonyl (C=O) that its substituting group is selected from (C1-C6)-alkoxyl group and halogen and X.
4, as each claimed compounds of claim 1 to 3, it is as medicine.
5, be used to control Mammals, the particularly purposes of human tumor illness as each claimed compounds of claim 1 to 3.
6, medicine, it comprises at least a as each claimed compounds of claim 1 to 3 and pharmaceutically acceptable auxiliary, thinner and/or carrier.
7, the method for preparation I compound,
Wherein A, B, C, D, R1, R2, R3, R4, R4, R5, X, Y, Z and n such as claim 1 definition, it is characterized in that
B) make following formula ketone
With aa) oxime or bb) hydrazine derivative H2N-NH-R7 reaction, wherein R7 such as claim 1 definition, and make products therefrom and activatory carbonyl, sulfoxide or sulfonyl-derivatives cyclisation,
Perhaps with cc) phenyl acetic acid derivatives X1-CO-CH2-R8 reaction, wherein X1 is the leavings group that is fit to, for example halogen or (C1-C2)-alkoxyl group, and R8 such as claim 1 definition, cyclisation in the presence of alkali then.
Applications Claiming Priority (2)
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DE10143079.5 | 2001-09-03 | ||
DE10143079A DE10143079A1 (en) | 2001-09-03 | 2001-09-03 | Cyclic indole and heteroindole derivatives, their production and use as medicines |
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ID=32239891
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AR (1) | AR036776A1 (en) |
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CA (1) | CA2458399A1 (en) |
HU (1) | HUP0401446A3 (en) |
IL (1) | IL160441A0 (en) |
MX (1) | MXPA04002034A (en) |
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NZ (1) | NZ531642A (en) |
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CN111362891A (en) * | 2020-04-01 | 2020-07-03 | 杭州福斯特药业有限公司 | Production device and production method of acetyl tetrahydrofuran |
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2002
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- 2002-08-27 CA CA002458399A patent/CA2458399A1/en not_active Abandoned
- 2002-08-27 HU HU0401446A patent/HUP0401446A3/en unknown
- 2002-08-27 KR KR10-2004-7003201A patent/KR20040029463A/en not_active Application Discontinuation
- 2002-08-27 PL PL02370210A patent/PL370210A1/en not_active Application Discontinuation
- 2002-08-27 JP JP2003525001A patent/JP2005508898A/en not_active Withdrawn
- 2002-08-27 NZ NZ531642A patent/NZ531642A/en unknown
- 2002-08-27 IL IL16044102A patent/IL160441A0/en unknown
- 2002-08-27 EP EP02767436A patent/EP1423393A1/en not_active Withdrawn
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CN111362891A (en) * | 2020-04-01 | 2020-07-03 | 杭州福斯特药业有限公司 | Production device and production method of acetyl tetrahydrofuran |
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PL370210A1 (en) | 2005-05-16 |
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MXPA04002034A (en) | 2004-07-08 |
IL160441A0 (en) | 2004-07-25 |
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BR0212300A (en) | 2004-10-13 |
AR036776A1 (en) | 2004-10-06 |
HUP0401446A2 (en) | 2004-11-29 |
HUP0401446A3 (en) | 2006-11-28 |
CA2458399A1 (en) | 2003-03-13 |
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