NO841958L - Nye indolforbindelser - Google Patents

Info

Publication number

NO841958L

NO841958L NO841958A NO841958A NO841958L NO 841958 L NO841958 L NO 841958L NO 841958 A NO841958 A NO 841958A NO 841958 A NO841958 A NO 841958A NO 841958 L NO841958 L NO 841958L

Authority

NO

Norway

Prior art keywords

formula

pyridyl

compound

indole

compounds

Prior art date

1983-05-17

Links

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• 150000001875 compounds Chemical class 0.000 claims description 184
• -1 ♦ lower alkyl-(thio Chemical group 0.000 claims description 117
• 150000003839 salts Chemical class 0.000 claims description 62
• 238000000034 method Methods 0.000 claims description 59
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 55
• 125000004432 carbon atom Chemical group C* 0.000 claims description 48
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 29
• 239000000203 mixture Substances 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000002947 alkylene group Chemical group 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 125000004450 alkenylene group Chemical group 0.000 claims description 14
• 230000008569 process Effects 0.000 claims description 14
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• UETRKVDAHIACJW-UHFFFAOYSA-N 5-(1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound C12=CC=CC=C2C(CCCCC(=O)O)=CN1C1=CC=CN=C1 UETRKVDAHIACJW-UHFFFAOYSA-N 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000004419 alkynylene group Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
• MCAPFZFMMUIMEH-UHFFFAOYSA-N 5-(2-methyl-1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound CC1=C(CCCCC(O)=O)C2=CC=CC=C2N1C1=CC=CN=C1 MCAPFZFMMUIMEH-UHFFFAOYSA-N 0.000 claims description 5
• 125000005678 ethenylene group Chemical class [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• VSKZGHVPGOMFAV-UHFFFAOYSA-N 1-pyridin-2-ylindole Chemical class C1=CC2=CC=CC=C2N1C1=CC=CC=N1 VSKZGHVPGOMFAV-UHFFFAOYSA-N 0.000 claims description 3
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
• 125000001589 carboacyl group Chemical group 0.000 claims description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• VMYNZSGRXMWFQI-UHFFFAOYSA-N 3-(1-pyridin-3-ylindol-3-yl)propanoic acid Chemical compound C12=CC=CC=C2C(CCC(=O)O)=CN1C1=CC=CN=C1 VMYNZSGRXMWFQI-UHFFFAOYSA-N 0.000 claims description 2
• YVXYWIWZAIGTAP-UHFFFAOYSA-N 5-(5-chloro-1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound C12=CC=C(Cl)C=C2C(CCCCC(=O)O)=CN1C1=CC=CN=C1 YVXYWIWZAIGTAP-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000002452 interceptive effect Effects 0.000 claims description 2
• 239000000463 material Substances 0.000 claims description 2
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
• 150000001721 carbon Chemical group 0.000 claims 2
• GUXQOVBGUZZBPJ-NSIKDUERSA-N (z)-2-methyl-5-(1-pyridin-3-ylindol-3-yl)pent-2-enoic acid Chemical compound C12=CC=CC=C2C(CC/C=C(/C)C(O)=O)=CN1C1=CC=CN=C1 GUXQOVBGUZZBPJ-NSIKDUERSA-N 0.000 claims 1
• UABNOBPFYCXKEW-UHFFFAOYSA-N 6-(1-pyridin-3-ylindol-3-yl)hexanoic acid Chemical compound C12=CC=CC=C2C(CCCCCC(=O)O)=CN1C1=CC=CN=C1 UABNOBPFYCXKEW-UHFFFAOYSA-N 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 230000001052 transient effect Effects 0.000 claims 1
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
• 239000000243 solution Substances 0.000 description 78
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
• 239000011541 reaction mixture Substances 0.000 description 40
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
• 239000003921 oil Substances 0.000 description 31
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
• 229910052740 iodine Inorganic materials 0.000 description 28
• 239000002585 base Substances 0.000 description 27
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
• 239000002253 acid Substances 0.000 description 25
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 25
• 239000007858 starting material Substances 0.000 description 25
• 238000009833 condensation Methods 0.000 description 24
• 230000005494 condensation Effects 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 238000006243 chemical reaction Methods 0.000 description 20
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
• 239000007787 solid Substances 0.000 description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
• 229910052757 nitrogen Inorganic materials 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• 125000005907 alkyl ester group Chemical group 0.000 description 13
• 125000004970 halomethyl group Chemical group 0.000 description 13
• 239000000543 intermediate Substances 0.000 description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
• 150000002148 esters Chemical class 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 239000012074 organic phase Substances 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• 238000001704 evaporation Methods 0.000 description 11
• 230000008020 evaporation Effects 0.000 description 11
• 239000000284 extract Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 11
• 229960000583 acetic acid Drugs 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
• 235000011054 acetic acid Nutrition 0.000 description 9
• 239000008346 aqueous phase Substances 0.000 description 9
• 230000005764 inhibitory process Effects 0.000 description 9
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
• 238000009835 boiling Methods 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 230000007062 hydrolysis Effects 0.000 description 8
• 238000006460 hydrolysis reaction Methods 0.000 description 8
• 239000012442 inert solvent Substances 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 239000012312 sodium hydride Substances 0.000 description 8
• 229910000104 sodium hydride Inorganic materials 0.000 description 8
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
• 108010069102 Thromboxane-A synthase Proteins 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 239000000377 silicon dioxide Substances 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
• 241000124008 Mammalia Species 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• 125000004423 acyloxy group Chemical group 0.000 description 6
• 229910052783 alkali metal Inorganic materials 0.000 description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
• NFLKJMSYUXZFDF-UHFFFAOYSA-N 1-pyridin-3-ylindole Chemical compound C1=CC2=CC=CC=C2N1C1=CC=CN=C1 NFLKJMSYUXZFDF-UHFFFAOYSA-N 0.000 description 5
• JHMUBQSCLBFHSR-UHFFFAOYSA-N 1-pyridin-3-ylindole-3-carbaldehyde Chemical compound C12=CC=CC=C2C(C=O)=CN1C1=CC=CN=C1 JHMUBQSCLBFHSR-UHFFFAOYSA-N 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
• 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 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 241000700159 Rattus Species 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• 230000002378 acidificating effect Effects 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 229940043279 diisopropylamine Drugs 0.000 description 5
• 125000000524 functional group Chemical group 0.000 description 5
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
• 230000003287 optical effect Effects 0.000 description 5
• 125000003431 oxalo group Chemical group 0.000 description 5
• KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 230000002285 radioactive effect Effects 0.000 description 5
• 235000019698 starch Nutrition 0.000 description 5
• PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 4
• SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
• QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 4
• 239000005751 Copper oxide Substances 0.000 description 4
• 239000007818 Grignard reagent Substances 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
• 239000013543 active substance Substances 0.000 description 4
• 150000001340 alkali metals Chemical class 0.000 description 4
• 125000004849 alkoxymethyl group Chemical group 0.000 description 4
• 150000001408 amides Chemical class 0.000 description 4
• 229910021529 ammonia Inorganic materials 0.000 description 4
• 150000003863 ammonium salts Chemical class 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• 229940114079 arachidonic acid Drugs 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• 239000000872 buffer Substances 0.000 description 4
• 150000001735 carboxylic acids Chemical class 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 229910000431 copper oxide Inorganic materials 0.000 description 4
• 125000004093 cyano group Chemical group *C#N 0.000 description 4
• XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 4
• 239000003480 eluent Substances 0.000 description 4
• 150000004795 grignard reagents Chemical class 0.000 description 4
• 238000011534 incubation Methods 0.000 description 4
• 150000002475 indoles Chemical class 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
• 239000011777 magnesium Substances 0.000 description 4
• 229910052749 magnesium Inorganic materials 0.000 description 4
• 229910052751 metal Inorganic materials 0.000 description 4
• 239000002184 metal Substances 0.000 description 4
• 150000007522 mineralic acids Chemical class 0.000 description 4
• 125000002524 organometallic group Chemical group 0.000 description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
• 238000003797 solvolysis reaction Methods 0.000 description 4
• 239000008107 starch Substances 0.000 description 4
• XNRNNGPBEPRNAR-JQBLCGNGSA-N thromboxane B2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O XNRNNGPBEPRNAR-JQBLCGNGSA-N 0.000 description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
• 229920002554 vinyl polymer Polymers 0.000 description 4
• AUNBMXVIRXVMHE-UHFFFAOYSA-N 1-phenyl-1-pyridin-3-ylhydrazine Chemical compound C=1C=CN=CC=1N(N)C1=CC=CC=C1 AUNBMXVIRXVMHE-UHFFFAOYSA-N 0.000 description 3
• DLQUYEDFKTVVRM-UHFFFAOYSA-N 3-(1-pyridin-3-ylindol-3-yl)propanal Chemical compound C12=CC=CC=C2C(CCC=O)=CN1C1=CC=CN=C1 DLQUYEDFKTVVRM-UHFFFAOYSA-N 0.000 description 3
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
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