NZ515556A - Purine derivatives, preparation method and pharmaceutical compositions containing same - Google Patents

Info

Publication number

NZ515556A

NZ515556A NZ515556A NZ51555600A NZ515556A NZ 515556 A NZ515556 A NZ 515556A NZ 515556 A NZ515556 A NZ 515556A NZ 51555600 A NZ51555600 A NZ 51555600A NZ 515556 A NZ515556 A NZ 515556A

Authority

NZ

New Zealand

Prior art keywords

radical

formula

compound

amino

radicals

Prior art date

1999-05-21

Links

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• 238000002360 preparation method Methods 0.000 title claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
• 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 2
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 2
• -1 -CH2-heterocyclyl Chemical group 0.000 claims abstract description 272
• 150000001875 compounds Chemical class 0.000 claims abstract description 245
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 79
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 34
• 125000003118 aryl group Chemical group 0.000 claims abstract description 33
• 239000002253 acid Substances 0.000 claims abstract description 28
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical group C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims abstract description 6
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
• 150000002367 halogens Chemical class 0.000 claims abstract description 5
• 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims abstract description 3
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims abstract 2
• 239000000047 product Substances 0.000 claims description 420
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 393
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 381
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 301
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 268
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 258
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 237
• 238000001035 drying Methods 0.000 claims description 213
• 239000012429 reaction media Substances 0.000 claims description 207
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 193
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 165
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 148
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 143
• 239000000377 silicon dioxide Substances 0.000 claims description 129
• 238000001704 evaporation Methods 0.000 claims description 127
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 110
• 150000003254 radicals Chemical class 0.000 claims description 106
• 125000004432 carbon atom Chemical group C* 0.000 claims description 105
• 238000005406 washing Methods 0.000 claims description 101
• 229910001868 water Inorganic materials 0.000 claims description 101
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 99
• 235000011114 ammonium hydroxide Nutrition 0.000 claims description 99
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 91
• VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 89
• 239000002904 solvent Substances 0.000 claims description 75
• 238000004587 chromatography analysis Methods 0.000 claims description 66
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
• 238000006243 chemical reaction Methods 0.000 claims description 57
• 230000002829 reductive effect Effects 0.000 claims description 51
• 238000013019 agitation Methods 0.000 claims description 48
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 34
• 239000011707 mineral Substances 0.000 claims description 34
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
• 239000003480 eluent Substances 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 19
• 150000007522 mineralic acids Chemical class 0.000 claims description 18
• 150000007524 organic acids Chemical class 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 150000007530 organic bases Chemical class 0.000 claims description 16
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
• 125000006239 protecting group Chemical group 0.000 claims description 16
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 238000000034 method Methods 0.000 claims description 15
• 235000005985 organic acids Nutrition 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 230000002927 anti-mitotic effect Effects 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
• 150000005840 aryl radicals Chemical class 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000003158 alcohol group Chemical group 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 150000002148 esters Chemical group 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 238000007254 oxidation reaction Methods 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 208000030852 Parasitic disease Diseases 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 5
• QZRPIDMTLGJZFA-IYARVYRRSA-N CCOC(=O)c1cccc(Nc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)c1 Chemical compound CCOC(=O)c1cccc(Nc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)c1 QZRPIDMTLGJZFA-IYARVYRRSA-N 0.000 claims description 5
• 241000233866 Fungi Species 0.000 claims description 5
• 150000001299 aldehydes Chemical class 0.000 claims description 5
• 238000002512 chemotherapy Methods 0.000 claims description 5
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 150000002576 ketones Chemical group 0.000 claims description 5
• 230000009223 neuronal apoptosis Effects 0.000 claims description 5
• 238000006722 reduction reaction Methods 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000004001 thioalkyl group Chemical group 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
• 230000002555 anti-neurodegenerative effect Effects 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 238000005886 esterification reaction Methods 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000001174 sulfone group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• KGIJGLXKUAZPFM-MXVIHJGJSA-N CCOC(=O)c1cc(Nc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc(c1)C(=O)OCC Chemical compound CCOC(=O)c1cc(Nc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc(c1)C(=O)OCC KGIJGLXKUAZPFM-MXVIHJGJSA-N 0.000 claims description 3
• WZUNHASDFCXWMZ-UAPYVXQJSA-N CCOC(=O)c1ccc(Nc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc1 Chemical compound CCOC(=O)c1ccc(Nc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc1 WZUNHASDFCXWMZ-UAPYVXQJSA-N 0.000 claims description 3
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
• 229910021529 ammonia Inorganic materials 0.000 claims description 3
• 238000003379 elimination reaction Methods 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 229910052739 hydrogen Inorganic materials 0.000 claims description 3
• 150000002923 oximes Chemical group 0.000 claims description 3
• 239000002244 precipitate Substances 0.000 claims description 3
• 238000007127 saponification reaction Methods 0.000 claims description 3
• NDPXFTYFCYCFRJ-UHFFFAOYSA-N 9-cyclopentylpurine-2,6-diamine trihydrochloride Chemical compound C1CCC(C1)N2C=NC3=C(N=C(N=C32)N)N.Cl.Cl.Cl NDPXFTYFCYCFRJ-UHFFFAOYSA-N 0.000 claims description 2
• RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 claims description 2
• MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims description 2
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 239000012948 isocyanate Substances 0.000 claims description 2
• 150000002513 isocyanates Chemical class 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
• 125000000565 sulfonamide group Chemical group 0.000 claims description 2
• 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 claims 1
• KIOOOXCGXZEAHK-UHFFFAOYSA-N 9-cyclopentylpurine-2,6-diamine dihydrochloride Chemical compound C1CCC(C1)N2C=NC3=C(N=C(N=C32)N)N.Cl.Cl KIOOOXCGXZEAHK-UHFFFAOYSA-N 0.000 claims 1
• BIULRBPHIVGVNR-WKILWMFISA-N N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2cc(cc(c2)C(O)=O)C(O)=O)c2ncn(C3CCCC3)c2n1 Chemical compound N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2cc(cc(c2)C(O)=O)C(O)=O)c2ncn(C3CCCC3)c2n1 BIULRBPHIVGVNR-WKILWMFISA-N 0.000 claims 1
• FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 claims 1
• WSIMVVQCANWBHC-UHFFFAOYSA-N ethyl 3-[[(2-chloro-9-cyclopentylpurin-6-yl)amino]methyl]benzoate Chemical compound CCOC(=O)C1=CC=CC(CNC=2C=3N=CN(C=3N=C(Cl)N=2)C2CCCC2)=C1 WSIMVVQCANWBHC-UHFFFAOYSA-N 0.000 claims 1
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
• 230000001681 protective effect Effects 0.000 claims 1
• 150000007513 acids Chemical class 0.000 abstract description 8
• 239000000203 mixture Substances 0.000 abstract description 4
• 239000000543 intermediate Substances 0.000 abstract description 3
• 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 abstract 1
• 101100295741 Gallus gallus COR4 gene Proteins 0.000 abstract 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 109
• 239000013078 crystal Substances 0.000 description 87
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 86
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 75
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 74
• 239000000908 ammonium hydroxide Substances 0.000 description 73
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 66
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
• 238000000746 purification Methods 0.000 description 58
• 239000000243 solution Substances 0.000 description 45
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 32
• 239000007864 aqueous solution Substances 0.000 description 31
• 239000011780 sodium chloride Substances 0.000 description 30
• 238000001914 filtration Methods 0.000 description 27
• 235000010755 mineral Nutrition 0.000 description 23
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 22
• 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 20
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 18
• 229910000024 caesium carbonate Inorganic materials 0.000 description 16
• 230000009471 action Effects 0.000 description 15
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 14
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 13
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
• BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
• YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 9
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 9
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 7
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 7
• 229910017974 NH40H Inorganic materials 0.000 description 7
• 206010028980 Neoplasm Diseases 0.000 description 7
• 238000007865 diluting Methods 0.000 description 7
• AQBJGAUQEJFPKZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CN)C=C1 AQBJGAUQEJFPKZ-UHFFFAOYSA-N 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 238000006482 condensation reaction Methods 0.000 description 6
• 238000002329 infrared spectrum Methods 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
• 108091000080 Phosphotransferase Proteins 0.000 description 5
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
• 229960000643 adenine Drugs 0.000 description 5
• 230000006907 apoptotic process Effects 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 230000022131 cell cycle Effects 0.000 description 5
• 102000020233 phosphotransferase Human genes 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 4
• IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 4
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
• 239000005711 Benzoic acid Substances 0.000 description 4
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