EA002347B1 - Замещенные трициклические соединения - Google Patents

Info

Publication number

EA002347B1

EA002347B1 EA199900301A EA199900301A EA002347B1 EA 002347 B1 EA002347 B1 EA 002347B1 EA 199900301 A EA199900301 A EA 199900301A EA 199900301 A EA199900301 A EA 199900301A EA 002347 B1 EA002347 B1 EA 002347B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

carbamoylcarbazol

hydroxyacetic acid

alkyl

phenyl

Prior art date

1998-04-17

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 204
• -1 phenoxy, benzyl Chemical group 0.000 claims abstract description 3236
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 223
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 204
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 100
• 239000002253 acid Substances 0.000 claims abstract description 91
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 82
• 150000002367 halogens Chemical class 0.000 claims abstract description 82
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 78
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 74
• 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
• 239000001257 hydrogen Substances 0.000 claims abstract description 42
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 41
• 125000001424 substituent group Chemical group 0.000 claims abstract description 31
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 24
• 125000002541 furyl group Chemical group 0.000 claims abstract description 23
• 239000000651 prodrug Substances 0.000 claims abstract description 23
• 229940002612 prodrug Drugs 0.000 claims abstract description 23
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims abstract description 16
• 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 16
• 230000003287 optical effect Effects 0.000 claims abstract description 15
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 14
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 14
• 239000012453 solvate Substances 0.000 claims abstract description 14
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
• LDPRPCQCLNSMAO-UHFFFAOYSA-N 9h-carbazole-4-carboxamide Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2C(=O)N LDPRPCQCLNSMAO-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
• ISRGSXVOKPRVIP-UHFFFAOYSA-N 9-benzyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-4-carbohydrazide Chemical compound C12=CC(OC)=CC(OC)=C2C=2C(C(=O)NN)CCCC=2N1CC1=CC=CC=C1 ISRGSXVOKPRVIP-UHFFFAOYSA-N 0.000 claims abstract description 4
• YSYSKDYLPVNKKJ-UHFFFAOYSA-N 9-benzyl-5-(cyanomethoxy)-7-methoxycarbazole-4-carboxamide Chemical compound C=1C(OC)=CC(OCC#N)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 YSYSKDYLPVNKKJ-UHFFFAOYSA-N 0.000 claims abstract description 4
• PTOFERBJZMNRQD-UHFFFAOYSA-N 9-benzyl-5-(cyanomethoxy)-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C12=CC(OC)=CC(OCC#N)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 PTOFERBJZMNRQD-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 9
• CGZZUCYZEGYRAT-UHFFFAOYSA-N 9-benzyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C12=CC(OC)=CC(OC)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 CGZZUCYZEGYRAT-UHFFFAOYSA-N 0.000 claims abstract 3
• HKMIHHJQMSJGKA-UHFFFAOYSA-N 9-benzyl-7-methoxy-5-(2h-tetrazol-5-ylmethoxy)carbazole-4-carboxamide Chemical compound C=1C=CC=CC=1CN1C2=CC=CC(C(N)=O)=C2C=2C1=CC(OC)=CC=2OCC1=NN=NN1 HKMIHHJQMSJGKA-UHFFFAOYSA-N 0.000 claims abstract 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract 2
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims abstract 2
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims abstract 2
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims abstract 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 344
• 229960004275 glycolic acid Drugs 0.000 claims description 219
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 116
• GSJFXBNYJCXDGI-UHFFFAOYSA-N methyl 2-hydroxyacetate Chemical compound COC(=O)CO GSJFXBNYJCXDGI-UHFFFAOYSA-N 0.000 claims description 77
• 238000006243 chemical reaction Methods 0.000 claims description 32
• 238000002360 preparation method Methods 0.000 claims description 28
• 238000000034 method Methods 0.000 claims description 21
• 125000006239 protecting group Chemical group 0.000 claims description 21
• 239000002168 alkylating agent Substances 0.000 claims description 15
• 229940100198 alkylating agent Drugs 0.000 claims description 15
• 239000013256 coordination polymer Substances 0.000 claims description 13
• 150000003536 tetrazoles Chemical group 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• 206010003246 arthritis Diseases 0.000 claims description 7
• GRNUVEMCUGCDDO-UHFFFAOYSA-N methyl 7-methyl-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(C)CC(=O)C2=C1NC1=C2C(C(=O)OC)=CC=C1 GRNUVEMCUGCDDO-UHFFFAOYSA-N 0.000 claims description 7
• WINGEFIITRDOLJ-UHFFFAOYSA-N tert-butyl 2-hydroxyacetate Chemical compound CC(C)(C)OC(=O)CO WINGEFIITRDOLJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 6
• FBELQXBIHJGQRS-UHFFFAOYSA-N 5-hydroxy-7-methyl-9-[(3-methylphenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC(C)=CC(O)=C3C3=C(C(N)=O)C=CC=C32)=C1 FBELQXBIHJGQRS-UHFFFAOYSA-N 0.000 claims description 5
• 208000036487 Arthropathies Diseases 0.000 claims description 5
• 208000012659 Joint disease Diseases 0.000 claims description 5
• 230000020335 dealkylation Effects 0.000 claims description 5
• 238000006900 dealkylation reaction Methods 0.000 claims description 5
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
• HTSWKDOXMSFQPB-UHFFFAOYSA-N 8-ethoxy-7-methoxy-9H-carbazole-4-carboxamide Chemical compound N1C2=CC=CC(C(N)=O)=C2C2=C1C(OCC)=C(OC)C=C2 HTSWKDOXMSFQPB-UHFFFAOYSA-N 0.000 claims description 4
• BUHJARZXNJGYSY-UHFFFAOYSA-N 9-[(3-fluorophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxamide Chemical compound C=1C(C)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC(F)=C1 BUHJARZXNJGYSY-UHFFFAOYSA-N 0.000 claims description 4
• JJVLMOAZPALOBR-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-[4-(trifluoromethyl)phenyl]carbazole-4-carboxamide Chemical compound C12=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 JJVLMOAZPALOBR-UHFFFAOYSA-N 0.000 claims description 4
• 206010006448 Bronchiolitis Diseases 0.000 claims description 4
• 206010040070 Septic Shock Diseases 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 206010006451 bronchitis Diseases 0.000 claims description 4
• 230000032050 esterification Effects 0.000 claims description 4
• 238000005886 esterification reaction Methods 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• PFNZJCITVCCGNP-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-9-[(3-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 PFNZJCITVCCGNP-UHFFFAOYSA-N 0.000 claims description 4
• OSLFZPFTEOMXPS-UHFFFAOYSA-N methyl 5-oxo-7-[4-(trifluoromethyl)phenyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=C(C(F)(F)F)C=C1 OSLFZPFTEOMXPS-UHFFFAOYSA-N 0.000 claims description 4
• LQLQHQVSCDFJIP-UHFFFAOYSA-N methyl 7-methyl-9-[(3-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 LQLQHQVSCDFJIP-UHFFFAOYSA-N 0.000 claims description 4
• SNOCNJSDASZTKU-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 SNOCNJSDASZTKU-UHFFFAOYSA-N 0.000 claims description 4
• HBLQCKSZNTXTII-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 HBLQCKSZNTXTII-UHFFFAOYSA-N 0.000 claims description 4
• UWKQMTAHLXBKDM-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-[4-(trifluoromethyl)phenyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 UWKQMTAHLXBKDM-UHFFFAOYSA-N 0.000 claims description 4
• 230000009467 reduction Effects 0.000 claims description 4
• 238000007363 ring formation reaction Methods 0.000 claims description 4
• 230000036303 septic shock Effects 0.000 claims description 4
• GELSNBZFFJBDDC-UHFFFAOYSA-N 1-ethoxy-7-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxamide Chemical compound C(C)OC1CCC(C=2C3=CC=C(C=C3NC1=2)OC)C(=O)N GELSNBZFFJBDDC-UHFFFAOYSA-N 0.000 claims description 3
• UWKXRBQTRAGVFQ-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-methoxy-5,6,7,8-tetrahydrocarbazol-4-yl)-2-hydroxyacetic acid Chemical compound COC1=CC(=C2C(=C1)N(C3=C2C(CCC3)C(=O)N)CC4=CC=CC=C4)C(C(=O)O)O UWKXRBQTRAGVFQ-UHFFFAOYSA-N 0.000 claims description 3
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
• 206010020877 Hypertrophic osteoarthropathy Diseases 0.000 claims description 3
• 206010033645 Pancreatitis Diseases 0.000 claims description 3
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
• 206010044541 Traumatic shock Diseases 0.000 claims description 3
• 201000010105 allergic rhinitis Diseases 0.000 claims description 3
• 238000005576 amination reaction Methods 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 239000011575 calcium Substances 0.000 claims description 3
• 229910052791 calcium Inorganic materials 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 230000003301 hydrolyzing effect Effects 0.000 claims description 3
• 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 3
• UNVNCIUTBUGNTR-UHFFFAOYSA-N methyl 5-hydroxy-9-[[2-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F UNVNCIUTBUGNTR-UHFFFAOYSA-N 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• 208000002574 reactive arthritis Diseases 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 159000000000 sodium salts Chemical class 0.000 claims description 3
• 208000011580 syndromic disease Diseases 0.000 claims description 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
• CZBVTBWZOBMOJJ-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-methoxycarbazol-4-yl)-2-hydroxyacetic acid Chemical compound COC1=CC(=C2C(=C1)N(C3=CC=CC(=C32)C(=O)N)CC4=CC=CC=C4)C(C(=O)O)O CZBVTBWZOBMOJJ-UHFFFAOYSA-N 0.000 claims description 2
• FLGCKKIRQATWRL-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoylcarbazol-4-yl)-2-hydroxyacetic acid Chemical compound C1=CC=C(C=C1)CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)O)O FLGCKKIRQATWRL-UHFFFAOYSA-N 0.000 claims description 2
• GIJITUQEJWSBRI-UHFFFAOYSA-N 5-hydroxy-9-[(2-methylphenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=CC=CC=C1CN1C2=CC=CC(C(N)=O)=C2C2=C(O)C=CC=C21 GIJITUQEJWSBRI-UHFFFAOYSA-N 0.000 claims description 2
• KQXAXQGJCMZYBA-UHFFFAOYSA-N 5-hydroxy-9-[(3-methylphenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(=C3C3=C(O)C=CC=C32)C(N)=O)=C1 KQXAXQGJCMZYBA-UHFFFAOYSA-N 0.000 claims description 2
• VXCYQLJSFFVGMX-UHFFFAOYSA-N 5-hydroxy-9-[(3-phenoxyphenyl)methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 VXCYQLJSFFVGMX-UHFFFAOYSA-N 0.000 claims description 2
• MSRUWXVJOFPJQK-UHFFFAOYSA-N 5-hydroxy-9-[[2-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F MSRUWXVJOFPJQK-UHFFFAOYSA-N 0.000 claims description 2
• TUWSXUGAOWLTNQ-UHFFFAOYSA-N 5-hydroxy-9-[[3-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 TUWSXUGAOWLTNQ-UHFFFAOYSA-N 0.000 claims description 2
• GBTJVHADNGRQBQ-UHFFFAOYSA-N 5-methoxy-8-methyl-9h-carbazole-4-carboxamide Chemical compound N1C2=CC=CC(C(N)=O)=C2C2=C1C(C)=CC=C2OC GBTJVHADNGRQBQ-UHFFFAOYSA-N 0.000 claims description 2
• PTMODKWZACRSDF-UHFFFAOYSA-N 8-chloro-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound N1C2=C(Cl)C=CC(O)=C2C2=C1C=CC=C2C(=O)N PTMODKWZACRSDF-UHFFFAOYSA-N 0.000 claims description 2
• HCWHUTCSDPMTFK-UHFFFAOYSA-N 9-[(2-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1Cl HCWHUTCSDPMTFK-UHFFFAOYSA-N 0.000 claims description 2
• ATFZXISCTBMYTH-UHFFFAOYSA-N 9-[(2-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1C#N ATFZXISCTBMYTH-UHFFFAOYSA-N 0.000 claims description 2
• SRAJNLCQHFQSIZ-UHFFFAOYSA-N 9-[(2-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1F SRAJNLCQHFQSIZ-UHFFFAOYSA-N 0.000 claims description 2
• MONOOOZJWVXGHQ-UHFFFAOYSA-N 9-[(3-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(Cl)=C1 MONOOOZJWVXGHQ-UHFFFAOYSA-N 0.000 claims description 2
• MXEREPIUEWGBPA-UHFFFAOYSA-N 9-[(3-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(C#N)=C1 MXEREPIUEWGBPA-UHFFFAOYSA-N 0.000 claims description 2
• ALXSLILFYVMFEJ-UHFFFAOYSA-N 9-[(3-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(F)=C1 ALXSLILFYVMFEJ-UHFFFAOYSA-N 0.000 claims description 2
• MAWQJLBAPRFZIH-UHFFFAOYSA-N 9-benzyl-5,7-dimethoxycarbazole-4-carboxamide Chemical compound C=1C(OC)=CC(OC)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 MAWQJLBAPRFZIH-UHFFFAOYSA-N 0.000 claims description 2
• ILIKMDNKNZVOMD-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-methoxycarbazole-4-carboxamide Chemical compound C=1C(OC)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 ILIKMDNKNZVOMD-UHFFFAOYSA-N 0.000 claims description 2
• HXESYJXBJORHDW-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-pentylcarbazole-4-carboxamide Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 HXESYJXBJORHDW-UHFFFAOYSA-N 0.000 claims description 2
• PSDHESHUDOJGBM-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-phenylcarbazole-4-carboxamide Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 PSDHESHUDOJGBM-UHFFFAOYSA-N 0.000 claims description 2
• FMEIHIOTBPUOIJ-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-propan-2-ylcarbazole-4-carboxamide Chemical compound C=1C(C(C)C)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 FMEIHIOTBPUOIJ-UHFFFAOYSA-N 0.000 claims description 2
• FJGZTTJYTQDFHV-UHFFFAOYSA-N 9-benzyl-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 FJGZTTJYTQDFHV-UHFFFAOYSA-N 0.000 claims description 2
• SSKLUMQEAPFGGT-UHFFFAOYSA-N 9-benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OC)=CC=C(C)C=2N1CC1=CC=CC=C1 SSKLUMQEAPFGGT-UHFFFAOYSA-N 0.000 claims description 2
• ODJLEHJTAOFQHI-UHFFFAOYSA-N 9-benzyl-5-methoxy-8-methylcarbazole-4-carboxamide Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OC)=CC=C(C)C=2N1CC1=CC=CC=C1 ODJLEHJTAOFQHI-UHFFFAOYSA-N 0.000 claims description 2
• GWSIUDSDXNVENV-UHFFFAOYSA-N 9-benzyl-7-(4-chlorophenyl)-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 GWSIUDSDXNVENV-UHFFFAOYSA-N 0.000 claims description 2
• CVMPWOFIAOZART-UHFFFAOYSA-N 9-benzyl-8-chloro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OC)=CC=C(Cl)C=2N1CC1=CC=CC=C1 CVMPWOFIAOZART-UHFFFAOYSA-N 0.000 claims description 2
• PBCJGXMQHNIUPD-UHFFFAOYSA-N 9-benzyl-8-chloro-5-methoxycarbazole-4-carboxamide Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OC)=CC=C(Cl)C=2N1CC1=CC=CC=C1 PBCJGXMQHNIUPD-UHFFFAOYSA-N 0.000 claims description 2
• XABCYFUHAKJZCS-UHFFFAOYSA-N 9-benzyl-8-fluoro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OC)=CC=C(F)C=2N1CC1=CC=CC=C1 XABCYFUHAKJZCS-UHFFFAOYSA-N 0.000 claims description 2
• DVQREHPZPZCGLD-UHFFFAOYSA-N 9-benzyl-8-fluoro-5-methoxycarbazole-4-carboxamide Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OC)=CC=C(F)C=2N1CC1=CC=CC=C1 DVQREHPZPZCGLD-UHFFFAOYSA-N 0.000 claims description 2
• 206010000599 Acromegaly Diseases 0.000 claims description 2
• 208000008190 Agammaglobulinemia Diseases 0.000 claims description 2
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
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• CKCXDPOPQOSCJA-UHFFFAOYSA-N CC1=CC(=CC=C1)CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)OC)O Chemical compound CC1=CC(=CC=C1)CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)OC)O CKCXDPOPQOSCJA-UHFFFAOYSA-N 0.000 claims description 2
• KTEHPEYHRRITND-UHFFFAOYSA-N COC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4=CC(=CC=C4)C(F)(F)F)O Chemical compound COC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4=CC(=CC=C4)C(F)(F)F)O KTEHPEYHRRITND-UHFFFAOYSA-N 0.000 claims description 2
• ARIIWZKYQZQXQE-UHFFFAOYSA-N COC(C(O)C1=CC=CC=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=C(C=CC=C1)C)=O Chemical compound COC(C(O)C1=CC=CC=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=C(C=CC=C1)C)=O ARIIWZKYQZQXQE-UHFFFAOYSA-N 0.000 claims description 2
• LKHQJWJSNRKGKY-UHFFFAOYSA-N COC(C(O)C1=CC=CC=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=CC=CC=C1)=O Chemical compound COC(C(O)C1=CC=CC=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=CC=CC=C1)=O LKHQJWJSNRKGKY-UHFFFAOYSA-N 0.000 claims description 2
• 206010008690 Chondrocalcinosis pyrophosphate Diseases 0.000 claims description 2
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• 206010020983 Hypogammaglobulinaemia Diseases 0.000 claims description 2
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• 208000033464 Reiter syndrome Diseases 0.000 claims description 2
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• 208000021240 acute bronchiolitis Diseases 0.000 claims description 2
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
• 210000000845 cartilage Anatomy 0.000 claims description 2
• 208000002849 chondrocalcinosis Diseases 0.000 claims description 2
• 208000007451 chronic bronchitis Diseases 0.000 claims description 2
• 230000001684 chronic effect Effects 0.000 claims description 2
• 239000013078 crystal Substances 0.000 claims description 2
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• 230000008021 deposition Effects 0.000 claims description 2
• MOZDUONUZZHNHY-UHFFFAOYSA-N ethyl 2-(9-benzyl-5-carbamoyl-2-methoxy-5,6,7,8-tetrahydrocarbazol-4-yl)-2-hydroxyacetate Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(C(O)C(=O)OCC)=CC(OC)=CC=2N1CC1=CC=CC=C1 MOZDUONUZZHNHY-UHFFFAOYSA-N 0.000 claims description 2
• NTTXCAMHFZZOTH-UHFFFAOYSA-N ethyl 5-methoxy-8-methyl-2,3,4,9-tetrahydro-1h-carbazole-4-carboxylate Chemical compound N1C2=C(C)C=CC(OC)=C2C2=C1CCCC2C(=O)OCC NTTXCAMHFZZOTH-UHFFFAOYSA-N 0.000 claims description 2
• UDRZOTKSRMNJBZ-UHFFFAOYSA-N ethyl 9-benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylate Chemical compound CCOC(=O)C1CCCC2=C1C1=C(OC)C=CC(C)=C1N2CC1=CC=CC=C1 UDRZOTKSRMNJBZ-UHFFFAOYSA-N 0.000 claims description 2
• AANXBKIMDTVFQA-UHFFFAOYSA-N ethyl 9-benzyl-8-chloro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylate Chemical compound CCOC(=O)C1CCCC2=C1C1=C(OC)C=CC(Cl)=C1N2CC1=CC=CC=C1 AANXBKIMDTVFQA-UHFFFAOYSA-N 0.000 claims description 2
• SWWDNZRFRCJACD-UHFFFAOYSA-N ethyl 9-benzyl-8-fluoro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylate Chemical compound CCOC(=O)C1CCCC2=C1C1=C(OC)C=CC(F)=C1N2CC1=CC=CC=C1 SWWDNZRFRCJACD-UHFFFAOYSA-N 0.000 claims description 2
• 208000034737 hemoglobinopathy Diseases 0.000 claims description 2
• 208000020346 hyperlipoproteinemia Diseases 0.000 claims description 2
• 208000014674 injury Diseases 0.000 claims description 2
• 230000000366 juvenile effect Effects 0.000 claims description 2
• DWIAYAAEVRBFGW-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C DWIAYAAEVRBFGW-UHFFFAOYSA-N 0.000 claims description 2
• ZEMCNOHCNUFOAM-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-phenoxyphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 ZEMCNOHCNUFOAM-UHFFFAOYSA-N 0.000 claims description 2
• QOPNWBDBQJGPAE-UHFFFAOYSA-N methyl 5-hydroxy-9-[[3-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 QOPNWBDBQJGPAE-UHFFFAOYSA-N 0.000 claims description 2
• YAQSQUUCVARXHF-UHFFFAOYSA-N methyl 5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CCC(=O)C2=C1NC1=C2C(C(=O)OC)=CC=C1 YAQSQUUCVARXHF-UHFFFAOYSA-N 0.000 claims description 2
• WAUGXTPQYOKHNZ-UHFFFAOYSA-N methyl 5-oxo-7-pentyl-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound N1C2=CC=CC(C(=O)OC)=C2C2=C1CC(CCCCC)CC2=O WAUGXTPQYOKHNZ-UHFFFAOYSA-N 0.000 claims description 2
• KXTFYUZQWPILHJ-UHFFFAOYSA-N methyl 5-oxo-7-phenyl-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=CC=C1 KXTFYUZQWPILHJ-UHFFFAOYSA-N 0.000 claims description 2
• YDTQOOFEQXDLDW-UHFFFAOYSA-N methyl 5-oxo-7-propan-2-yl-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(C(C)C)CC(=O)C2=C1NC1=C2C(C(=O)OC)=CC=C1 YDTQOOFEQXDLDW-UHFFFAOYSA-N 0.000 claims description 2
• YTCCWBPOFPFFCR-UHFFFAOYSA-N methyl 5-oxo-9-[(3-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 YTCCWBPOFPFFCR-UHFFFAOYSA-N 0.000 claims description 2
• PEPCSOVPNMWRKL-UHFFFAOYSA-N methyl 5-oxo-9-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 PEPCSOVPNMWRKL-UHFFFAOYSA-N 0.000 claims description 2
• LALRTWKTWDFFIX-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=C(Cl)C=C1 LALRTWKTWDFFIX-UHFFFAOYSA-N 0.000 claims description 2
• XTYILSXHCGTKHW-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl XTYILSXHCGTKHW-UHFFFAOYSA-N 0.000 claims description 2
• ZYVPKFGMYOFKST-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl ZYVPKFGMYOFKST-UHFFFAOYSA-N 0.000 claims description 2
• HIEJYFQOXJHYHA-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N HIEJYFQOXJHYHA-UHFFFAOYSA-N 0.000 claims description 2
• FIORTLXKZVVDKE-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N FIORTLXKZVVDKE-UHFFFAOYSA-N 0.000 claims description 2
• ZFFJJZQSUVMMOI-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F ZFFJJZQSUVMMOI-UHFFFAOYSA-N 0.000 claims description 2
• XFHQZLZSUZCKLV-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F XFHQZLZSUZCKLV-UHFFFAOYSA-N 0.000 claims description 2
• WBHWSVHRGPRIAZ-UHFFFAOYSA-N methyl 9-[(2-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C WBHWSVHRGPRIAZ-UHFFFAOYSA-N 0.000 claims description 2
• QLXRVTDGPVGHFD-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 QLXRVTDGPVGHFD-UHFFFAOYSA-N 0.000 claims description 2
• OEGIIJDSTAEKEM-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 OEGIIJDSTAEKEM-UHFFFAOYSA-N 0.000 claims description 2
• UXAWWFVDQJYGDY-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 UXAWWFVDQJYGDY-UHFFFAOYSA-N 0.000 claims description 2
• GGSHGRAQDSJBOY-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 GGSHGRAQDSJBOY-UHFFFAOYSA-N 0.000 claims description 2
• JSOLWPACLIOTBG-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 JSOLWPACLIOTBG-UHFFFAOYSA-N 0.000 claims description 2
• HXURTMLFEIDBBQ-UHFFFAOYSA-N methyl 9-[(3-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 HXURTMLFEIDBBQ-UHFFFAOYSA-N 0.000 claims description 2
• FNOKDIQYOIJIKH-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1 FNOKDIQYOIJIKH-UHFFFAOYSA-N 0.000 claims description 2
• PKFVGCGERGKRQI-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 PKFVGCGERGKRQI-UHFFFAOYSA-N 0.000 claims description 2
• VVVSZKHAZFQJHB-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 VVVSZKHAZFQJHB-UHFFFAOYSA-N 0.000 claims description 2
• LRAQLBIAAGYKIS-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 LRAQLBIAAGYKIS-UHFFFAOYSA-N 0.000 claims description 2
• ZHYOTVKRNRGRAI-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1 ZHYOTVKRNRGRAI-UHFFFAOYSA-N 0.000 claims description 2
• XFTAOPDANGNLBE-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 XFTAOPDANGNLBE-UHFFFAOYSA-N 0.000 claims description 2
• OAKDTHHXAYPQFO-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 OAKDTHHXAYPQFO-UHFFFAOYSA-N 0.000 claims description 2
• VWBPDQQZNOYORV-UHFFFAOYSA-N methyl 9-benzyl-7-(4-chlorophenyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 VWBPDQQZNOYORV-UHFFFAOYSA-N 0.000 claims description 2
• RACLAUSVCLNLIZ-UHFFFAOYSA-N methyl 9-benzyl-7-(4-chlorophenyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 RACLAUSVCLNLIZ-UHFFFAOYSA-N 0.000 claims description 2
• 230000002981 neuropathic effect Effects 0.000 claims description 2
• 201000008482 osteoarthritis Diseases 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 230000000306 recurrent effect Effects 0.000 claims description 2
• 208000007056 sickle cell anemia Diseases 0.000 claims description 2
• 201000005671 spondyloarthropathy Diseases 0.000 claims description 2
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
• 230000008733 trauma Effects 0.000 claims description 2
• 230000002152 alkylating effect Effects 0.000 claims 4
• HMCNXTMKWMOREW-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-5,6,7,8-tetrahydrocarbazol-4-yl)-2-hydroxyacetic acid Chemical compound C1CC(C2=C(C1)N(C3=CC=CC(=C32)C(C(=O)O)O)CC4=CC=CC=C4)C(=O)N HMCNXTMKWMOREW-UHFFFAOYSA-N 0.000 claims 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
• 208000004575 Infectious Arthritis Diseases 0.000 claims 2
• 239000003937 drug carrier Substances 0.000 claims 2
• NIRLBKXYTDHSFZ-UHFFFAOYSA-N methyl 2-bromo-3-[(4-methyl-6-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(C)CC=2)=O)=C1Br NIRLBKXYTDHSFZ-UHFFFAOYSA-N 0.000 claims 2
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 1
• COUNTPGXSHULJS-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-1-chlorocarbazol-4-yl)-2-hydroxyacetic acid Chemical compound C1=CC=C(C=C1)CN2C3=CC=CC(=C3C4=C(C=CC(=C42)Cl)C(C(=O)O)O)C(=O)N COUNTPGXSHULJS-UHFFFAOYSA-N 0.000 claims 1
• QIRYZCQFYKDMTI-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-1-fluoro-5,6,7,8-tetrahydrocarbazol-4-yl)-2-hydroxyacetic acid Chemical compound C1CC(C2=C(C1)N(C3=C(C=CC(=C23)C(C(=O)O)O)F)CC4=CC=CC=C4)C(=O)N QIRYZCQFYKDMTI-UHFFFAOYSA-N 0.000 claims 1
• RTJKZVDUSYOMQI-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-1-fluorocarbazol-4-yl)-2-hydroxyacetic acid Chemical compound C1=CC=C(C=C1)CN2C3=CC=CC(=C3C4=C(C=CC(=C42)F)C(C(=O)O)O)C(=O)N RTJKZVDUSYOMQI-UHFFFAOYSA-N 0.000 claims 1
• NETIWGOFLJSIJR-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-1-methyl-5,6,7,8-tetrahydrocarbazol-4-yl)-2-hydroxyacetic acid Chemical compound CC1=C2C(=C(C=C1)C(C(=O)O)O)C3=C(N2CC4=CC=CC=C4)CCCC3C(=O)N NETIWGOFLJSIJR-UHFFFAOYSA-N 0.000 claims 1
• APNWBPJFQWGJSH-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl)-2-hydroxyacetic acid Chemical compound CC1=C2C(=C(C=C1)C(C(=O)O)O)C3=C(C=CC=C3N2CC4=CC=CC=C4)C(=O)N APNWBPJFQWGJSH-UHFFFAOYSA-N 0.000 claims 1
• AJZUYGYKHMNPSA-UHFFFAOYSA-N 2-[5-carbamoyl-9-(cyclohexylmethyl)carbazol-4-yl]-2-hydroxyacetic acid Chemical compound C1CCC(CC1)CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)O)O AJZUYGYKHMNPSA-UHFFFAOYSA-N 0.000 claims 1
• XMFFUTJRVJNVAN-UHFFFAOYSA-N 2-[5-carbamoyl-9-(cyclopentylmethyl)carbazol-4-yl]-2-hydroxyacetic acid Chemical compound C1CCC(C1)CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)O)O XMFFUTJRVJNVAN-UHFFFAOYSA-N 0.000 claims 1
• GUPNYANXWGGEGR-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-methylphenyl)methyl]carbazol-4-yl]-2-hydroxyacetic acid Chemical compound CC1=CC=CC=C1CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)O)O GUPNYANXWGGEGR-UHFFFAOYSA-N 0.000 claims 1
• NUYSSGQUGSOQIY-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-fluorophenyl)methyl]carbazol-4-yl]-2-hydroxyacetic acid Chemical compound C1=CC(=CC(=C1)F)CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)O)O NUYSSGQUGSOQIY-UHFFFAOYSA-N 0.000 claims 1
• PMLKFUZGRZVPOE-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]-2-hydroxyacetic acid Chemical compound CC1=CC(=CC=C1)CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)O)O PMLKFUZGRZVPOE-UHFFFAOYSA-N 0.000 claims 1
• LQOPHNPAIIDQNW-UHFFFAOYSA-N 2-[5-carbamoyl-9-[[3-(trifluoromethyl)phenyl]methyl]carbazol-4-yl]-2-hydroxyacetic acid Chemical compound C1=CC(=CC(=C1)C(F)(F)F)CN2C3=CC=CC(=C3C4=C(C=CC=C42)C(=O)N)C(C(=O)O)O LQOPHNPAIIDQNW-UHFFFAOYSA-N 0.000 claims 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
• CTEFKDJTLSKQGU-UHFFFAOYSA-N 3,9-dihydrocarbazol-4-one Chemical compound N1C2=CC=CC=C2C2=C1C=CCC2=O CTEFKDJTLSKQGU-UHFFFAOYSA-N 0.000 claims 1
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
• NKVQLLVHAGAASU-UHFFFAOYSA-N 5-hydroxy-8-methyl-9H-carbazole-4-carboxamide Chemical compound CC1=CC=C(C=2C3=C(C=CC=C3NC1=2)C(N)=O)O NKVQLLVHAGAASU-UHFFFAOYSA-N 0.000 claims 1
• SFVXFRXONWSBOB-UHFFFAOYSA-N 5-hydroxy-9-[(3-iodophenyl)methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(I)=C1 SFVXFRXONWSBOB-UHFFFAOYSA-N 0.000 claims 1
• GLUGRMILFITQLF-UHFFFAOYSA-N 5-hydroxy-9-[[3-(trifluoromethoxy)phenyl]methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(OC(F)(F)F)=C1 GLUGRMILFITQLF-UHFFFAOYSA-N 0.000 claims 1
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• UBMXZDVSVAJNKR-UHFFFAOYSA-N 9-(cyclohexylmethyl)-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1CCCCC1 UBMXZDVSVAJNKR-UHFFFAOYSA-N 0.000 claims 1
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• JBUQLWZGSDWLNU-UHFFFAOYSA-N 9-benzyl-5-hydroxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C1=2C(C)=CC=C(O)C=2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 JBUQLWZGSDWLNU-UHFFFAOYSA-N 0.000 claims 1
• HQGXELDGYSMEAM-UHFFFAOYSA-N 9-benzyl-5-hydroxy-8-methylcarbazole-4-carboxamide Chemical compound CC1=CC=C(O)C(C2=C(C(N)=O)C=CC=C22)=C1N2CC1=CC=CC=C1 HQGXELDGYSMEAM-UHFFFAOYSA-N 0.000 claims 1
• GWCJQGNSWFHLCA-UHFFFAOYSA-N 9-benzyl-7-(furan-2-yl)-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC(C=3OC=CC=3)=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 GWCJQGNSWFHLCA-UHFFFAOYSA-N 0.000 claims 1
• XNLJSEOGTHOPTF-UHFFFAOYSA-N 9-benzyl-8-chloro-5-hydroxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound NC(=O)C1CCCC2=C1C1=C(O)C=CC(Cl)=C1N2CC1=CC=CC=C1 XNLJSEOGTHOPTF-UHFFFAOYSA-N 0.000 claims 1
• YMQFUKOKCIKSKX-UHFFFAOYSA-N 9-benzyl-8-fluoro-5-hydroxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound NC(=O)C1CCCC2=C1C1=C(O)C=CC(F)=C1N2CC1=CC=CC=C1 YMQFUKOKCIKSKX-UHFFFAOYSA-N 0.000 claims 1
• IWIQVLVTAFKPRR-UHFFFAOYSA-N 9-benzyl-8-fluoro-5-hydroxycarbazole-4-carboxamide Chemical compound C12=C(F)C=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 IWIQVLVTAFKPRR-UHFFFAOYSA-N 0.000 claims 1
• 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 claims 1
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• 206010006811 Bursitis Diseases 0.000 claims 1
• BVVBSYJVXSLXHH-UHFFFAOYSA-N CC(C)(C)OC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4=CC(=CC=C4)F)O Chemical compound CC(C)(C)OC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4=CC(=CC=C4)F)O BVVBSYJVXSLXHH-UHFFFAOYSA-N 0.000 claims 1
• GERHZFPOMFRYRS-UHFFFAOYSA-N COC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4=CC(=CC=C4)OC(F)(F)F)O Chemical compound COC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4=CC(=CC=C4)OC(F)(F)F)O GERHZFPOMFRYRS-UHFFFAOYSA-N 0.000 claims 1
• VPFSPRPLPUQCEA-UHFFFAOYSA-N COC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4CCCC4)O Chemical compound COC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4CCCC4)O VPFSPRPLPUQCEA-UHFFFAOYSA-N 0.000 claims 1
• XGZXAKWFCBNJPI-UHFFFAOYSA-N COC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4CCCCC4)O Chemical compound COC(=O)C(C1=C2C(=CC=C1)N(C3=CC=CC(=C32)C(=O)N)CC4CCCCC4)O XGZXAKWFCBNJPI-UHFFFAOYSA-N 0.000 claims 1
• WDQYTAXGMPMZDO-UHFFFAOYSA-N COC(=O)C(C1=C2C3=C(CCCC3C(=O)N)N(C2=C(C=C1)F)CC4=CC=CC=C4)O Chemical compound COC(=O)C(C1=C2C3=C(CCCC3C(=O)N)N(C2=C(C=C1)F)CC4=CC=CC=C4)O WDQYTAXGMPMZDO-UHFFFAOYSA-N 0.000 claims 1
• KKHBTHKDXTXAKP-UHFFFAOYSA-N COC(C(O)C1=CC=C(C=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=CC=CC=C1)C)=O Chemical compound COC(C(O)C1=CC=C(C=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=CC=CC=C1)C)=O KKHBTHKDXTXAKP-UHFFFAOYSA-N 0.000 claims 1
• JTVAASQEXOGYHL-UHFFFAOYSA-N COC(C(O)C1=CC=C(C=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=CC=CC=C1)F)=O Chemical compound COC(C(O)C1=CC=C(C=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=CC=CC=C1)F)=O JTVAASQEXOGYHL-UHFFFAOYSA-N 0.000 claims 1
• VGDZYWNHJSSQGT-UHFFFAOYSA-N COC(C(O)C1=CC=C(C=2NC3=CC=CC(=C3C12)C(N)=O)Cl)=O Chemical compound COC(C(O)C1=CC=C(C=2NC3=CC=CC(=C3C12)C(N)=O)Cl)=O VGDZYWNHJSSQGT-UHFFFAOYSA-N 0.000 claims 1
• 206010024238 Leptospirosis Diseases 0.000 claims 1
• 208000032514 Leukocytoclastic vasculitis Diseases 0.000 claims 1
• 208000016604 Lyme disease Diseases 0.000 claims 1
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
• 206010040047 Sepsis Diseases 0.000 claims 1
• 201000002661 Spondylitis Diseases 0.000 claims 1
• 206010047115 Vasculitis Diseases 0.000 claims 1
• 239000004914 cyclooctane Substances 0.000 claims 1
• 238000006356 dehydrogenation reaction Methods 0.000 claims 1
• 230000002538 fungal effect Effects 0.000 claims 1
• 230000002458 infectious effect Effects 0.000 claims 1
• 230000005764 inhibitory process Effects 0.000 claims 1
• 201000004990 juvenile ankylosing spondylitis Diseases 0.000 claims 1
• QCYHHHHOQGEKIE-UHFFFAOYSA-N methyl 2-(2-methoxyphenyl)-3-nitrobenzoate Chemical group COC(=O)C1=CC=CC([N+]([O-])=O)=C1C1=CC=CC=C1OC QCYHHHHOQGEKIE-UHFFFAOYSA-N 0.000 claims 1
• XUAYLFHKEMIAIW-UHFFFAOYSA-N methyl 2-bromo-3-[(6-oxo-4-pentylcyclohexen-1-yl)amino]benzoate Chemical compound O=C1CC(CCCCC)CC=C1NC1=CC=CC(C(=O)OC)=C1Br XUAYLFHKEMIAIW-UHFFFAOYSA-N 0.000 claims 1
• XEBMYTUXOYOVJN-UHFFFAOYSA-N methyl 2-bromo-3-[(6-oxo-4-phenylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(CC=2)C=2C=CC=CC=2)=O)=C1Br XEBMYTUXOYOVJN-UHFFFAOYSA-N 0.000 claims 1
• PPUUXYOKSGMPNS-UHFFFAOYSA-N methyl 2-bromo-3-[(6-oxo-4-propan-2-ylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(CC=2)C(C)C)=O)=C1Br PPUUXYOKSGMPNS-UHFFFAOYSA-N 0.000 claims 1
• IFEUCXUVVPNSIG-UHFFFAOYSA-N methyl 2-bromo-3-[(6-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCCC=2)=O)=C1Br IFEUCXUVVPNSIG-UHFFFAOYSA-N 0.000 claims 1
• JWLWCBBXKQCPJI-UHFFFAOYSA-N methyl 2-bromo-3-[[4-(4-chlorophenyl)-6-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(CC=2)C=2C=CC(Cl)=CC=2)=O)=C1Br JWLWCBBXKQCPJI-UHFFFAOYSA-N 0.000 claims 1
• AIVGQUAEBWAADU-UHFFFAOYSA-N methyl 2-bromo-3-[[4-(furan-2-yl)-6-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(CC=2)C=2OC=CC=2)=O)=C1Br AIVGQUAEBWAADU-UHFFFAOYSA-N 0.000 claims 1
• MDWRQJKKKDNNLG-UHFFFAOYSA-N methyl 2-bromo-3-[[4-(hydroxymethyl)-6-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(CO)CC=2)=O)=C1Br MDWRQJKKKDNNLG-UHFFFAOYSA-N 0.000 claims 1
• LDRKDSVFVSBAAT-UHFFFAOYSA-N methyl 2-chloro-3-[(6-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCCC=2)=O)=C1Cl LDRKDSVFVSBAAT-UHFFFAOYSA-N 0.000 claims 1
• TWOPOKNACRNJDU-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-iodophenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(I)=C1 TWOPOKNACRNJDU-UHFFFAOYSA-N 0.000 claims 1
• ZLSAMYFQRGMPFY-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 ZLSAMYFQRGMPFY-UHFFFAOYSA-N 0.000 claims 1
• LPGOWPXYSCNOID-UHFFFAOYSA-N methyl 5-hydroxy-9-[[3-(trifluoromethoxy)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(OC(F)(F)F)=C1 LPGOWPXYSCNOID-UHFFFAOYSA-N 0.000 claims 1
• CZQBMJBREUQSFG-UHFFFAOYSA-N methyl 5-methoxy-8-methyl-9H-carbazole-4-carboxylate Chemical compound CC1=CC=C(C=2C3=C(C=CC=C3NC1=2)C(=O)OC)OC CZQBMJBREUQSFG-UHFFFAOYSA-N 0.000 claims 1
• LLEOFYFCHLBTBJ-UHFFFAOYSA-N methyl 5-oxo-9-[[2-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F LLEOFYFCHLBTBJ-UHFFFAOYSA-N 0.000 claims 1
• YDADMHVBELPYRF-UHFFFAOYSA-N methyl 5-oxo-9-[[3-(trifluoromethoxy)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(OC(F)(F)F)=C1 YDADMHVBELPYRF-UHFFFAOYSA-N 0.000 claims 1
• SWIUIZXMNZTCRX-UHFFFAOYSA-N methyl 7-(hydroxymethyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(CO)CC(=O)C2=C1NC1=C2C(C(=O)OC)=CC=C1 SWIUIZXMNZTCRX-UHFFFAOYSA-N 0.000 claims 1
• FMMQJOKFRIRBOQ-UHFFFAOYSA-N methyl 8-benzyl-5-hydroxy-7-methyl-9h-carbazole-4-carboxylate Chemical compound CC1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1 FMMQJOKFRIRBOQ-UHFFFAOYSA-N 0.000 claims 1
• QPCSWIGFQVWSDE-UHFFFAOYSA-N methyl 8-benzyl-7-methyl-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound CC1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1 QPCSWIGFQVWSDE-UHFFFAOYSA-N 0.000 claims 1
• YLACHINBXBKUBX-UHFFFAOYSA-N methyl 9-(cyclohexylmethyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1CCCCC1 YLACHINBXBKUBX-UHFFFAOYSA-N 0.000 claims 1
• KISUBDQINFFPAU-UHFFFAOYSA-N methyl 9-(cyclohexylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1CCCCC1 KISUBDQINFFPAU-UHFFFAOYSA-N 0.000 claims 1
• HQXQUBSVHRBQAC-UHFFFAOYSA-N methyl 9-(cyclopentylmethyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1CCCC1 HQXQUBSVHRBQAC-UHFFFAOYSA-N 0.000 claims 1
• QZRSFEAXAOKXCG-UHFFFAOYSA-N methyl 9-(cyclopentylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1CCCC1 QZRSFEAXAOKXCG-UHFFFAOYSA-N 0.000 claims 1
• FFJIJEXTIQAHDU-UHFFFAOYSA-N methyl 9-[(2,3-difluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1F FFJIJEXTIQAHDU-UHFFFAOYSA-N 0.000 claims 1
• NZRDUNGWEBSXKX-UHFFFAOYSA-N methyl 9-[(2,3-difluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1F NZRDUNGWEBSXKX-UHFFFAOYSA-N 0.000 claims 1
• MQNNUYXCYBUUPW-UHFFFAOYSA-N methyl 9-[(2,6-dichlorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl MQNNUYXCYBUUPW-UHFFFAOYSA-N 0.000 claims 1
• GKDFGTVUWFSFSG-UHFFFAOYSA-N methyl 9-[(2,6-dichlorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl GKDFGTVUWFSFSG-UHFFFAOYSA-N 0.000 claims 1
• MRQKZMCJLKMCJL-UHFFFAOYSA-N methyl 9-[(2,6-difluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=C(F)C=CC=C1F MRQKZMCJLKMCJL-UHFFFAOYSA-N 0.000 claims 1
• NQJOZJJMFTYKAS-UHFFFAOYSA-N methyl 9-[(2,6-difluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=C(F)C=CC=C1F NQJOZJJMFTYKAS-UHFFFAOYSA-N 0.000 claims 1
• KYSDGKPVRQSADQ-UHFFFAOYSA-N methyl 9-[(3,5-dimethylphenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC(C)=CC(C)=C1 KYSDGKPVRQSADQ-UHFFFAOYSA-N 0.000 claims 1
• HCGFOPKRNGMOKA-UHFFFAOYSA-N methyl 9-[(3,5-dimethylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC(C)=CC(C)=C1 HCGFOPKRNGMOKA-UHFFFAOYSA-N 0.000 claims 1
• GKCQFBAIJMCCKA-UHFFFAOYSA-N methyl 9-[(3-iodophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(I)=C1 GKCQFBAIJMCCKA-UHFFFAOYSA-N 0.000 claims 1
• YMPIZZIWCULYFJ-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-[tri(propan-2-yl)silyloxymethyl]carbazole-4-carboxylate Chemical compound C12=CC(CO[Si](C(C)C)(C(C)C)C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 YMPIZZIWCULYFJ-UHFFFAOYSA-N 0.000 claims 1
• VJZMHAFNPNAFCS-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 VJZMHAFNPNAFCS-UHFFFAOYSA-N 0.000 claims 1
• HDDOVCMVRWRDTE-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-[tri(propan-2-yl)silyloxymethyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(CO[Si](C(C)C)(C(C)C)C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 HDDOVCMVRWRDTE-UHFFFAOYSA-N 0.000 claims 1
• IMOVFZJGDDTZJA-UHFFFAOYSA-N methyl 9-benzyl-7-(furan-2-yl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3OC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 IMOVFZJGDDTZJA-UHFFFAOYSA-N 0.000 claims 1
• IPCMTRGVYIHEOW-UHFFFAOYSA-N methyl 9-benzyl-7-(furan-2-yl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3OC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 IPCMTRGVYIHEOW-UHFFFAOYSA-N 0.000 claims 1
• CATQTVAHJGQIGC-UHFFFAOYSA-N methyl 9-benzyl-7-(hydroxymethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(CO)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 CATQTVAHJGQIGC-UHFFFAOYSA-N 0.000 claims 1
• 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
• 230000001575 pathological effect Effects 0.000 claims 1
• 201000006292 polyarteritis nodosa Diseases 0.000 claims 1
• 201000001223 septic arthritis Diseases 0.000 claims 1
• AAYKHTVNNLLGLP-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-methylcarbazol-4-yl)oxyacetic acid Chemical compound C=1C(C)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 AAYKHTVNNLLGLP-UHFFFAOYSA-N 0.000 abstract description 4
• 230000002452 interceptive effect Effects 0.000 abstract description 4
• OXQCZJHYRFSEQM-UHFFFAOYSA-N 2-[5-carbamoyl-2-methyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound CC1=CC=CC(CN2C3=CC(C)=CC(OCC(O)=O)=C3C3=C(C(N)=O)C=CC=C32)=C1 OXQCZJHYRFSEQM-UHFFFAOYSA-N 0.000 abstract description 3
• GSUXBSRHWJBQBV-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-fluorophenyl)methyl]-2-methylcarbazol-4-yl]oxyacetic acid Chemical compound C=1C(C)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC(F)=C1 GSUXBSRHWJBQBV-UHFFFAOYSA-N 0.000 abstract description 3
• 230000002378 acidificating effect Effects 0.000 abstract description 3
• XMNFDVRHTKIVQK-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-methoxycarbazol-4-yl)oxyacetic acid Chemical compound C=1C(OC)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 XMNFDVRHTKIVQK-UHFFFAOYSA-N 0.000 abstract description 2
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• PATZGVUJUUNVJN-UHFFFAOYSA-N 2-[5-carbamoyl-9-(naphthalen-1-ylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC=CC(OCC(O)=O)=C2C2=C1C=CC=C2C(=O)N PATZGVUJUUNVJN-UHFFFAOYSA-N 0.000 abstract description 2
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• HVKYETJTIUJSLB-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-chlorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1Cl HVKYETJTIUJSLB-UHFFFAOYSA-N 0.000 abstract description 2
• AKPJTFHUTNPVJJ-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-cyanophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1C#N AKPJTFHUTNPVJJ-UHFFFAOYSA-N 0.000 abstract description 2
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• LCPAHBQVBUXTEZ-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-cyanophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(C#N)=C1 LCPAHBQVBUXTEZ-UHFFFAOYSA-N 0.000 abstract description 2
• SKVCADFJTHKAEY-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-iodophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(I)=C1 SKVCADFJTHKAEY-UHFFFAOYSA-N 0.000 abstract description 2
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• FZCVOGNJZMDIQT-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-[4-(trifluoromethyl)phenyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 FZCVOGNJZMDIQT-UHFFFAOYSA-N 0.000 abstract description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 8
• 125000001475 halogen functional group Chemical group 0.000 abstract 7
• 229910006069 SO3H Inorganic materials 0.000 abstract 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 3
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• 125000006545 (C1-C9) alkyl group Chemical group 0.000 abstract 1
• YIWKRIZOIPDUPO-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl)oxyacetic acid Chemical compound CC1=CC=C(OCC(O)=O)C(C2=C(C(N)=O)C=CC=C22)=C1N2CC1=CC=CC=C1 YIWKRIZOIPDUPO-UHFFFAOYSA-N 0.000 abstract 1
• PPBJJWDNJPGZPF-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-pentylcarbazol-4-yl)oxyacetic acid Chemical compound C=1C(CCCCC)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 PPBJJWDNJPGZPF-UHFFFAOYSA-N 0.000 abstract 1
• CXRULWWTHRSJSP-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-1-chloro-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound NC(=O)C1CCCC2=C1C1=C(OCC(O)=O)C=CC(Cl)=C1N2CC1=CC=CC=C1 CXRULWWTHRSJSP-UHFFFAOYSA-N 0.000 abstract 1
• LUURCHSHYLGPEG-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-1-fluoro-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound NC(=O)C1CCCC2=C1C1=C(OCC(O)=O)C=CC(F)=C1N2CC1=CC=CC=C1 LUURCHSHYLGPEG-UHFFFAOYSA-N 0.000 abstract 1
• OCQARBMASQXXGZ-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-1-methyl-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound C1=2C(C)=CC=C(OCC(O)=O)C=2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 OCQARBMASQXXGZ-UHFFFAOYSA-N 0.000 abstract 1
• VZOLOKPKXHOJRH-UHFFFAOYSA-N 2-[5-carbamoyl-9-(pyridin-2-ylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=N1 VZOLOKPKXHOJRH-UHFFFAOYSA-N 0.000 abstract 1
• KQQRGQBJPMVABZ-UHFFFAOYSA-N 2-[5-carbamoyl-9-[[2-(trifluoromethyl)phenyl]methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F KQQRGQBJPMVABZ-UHFFFAOYSA-N 0.000 abstract 1
• XERTWWFWTYYSOP-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-(4-chlorophenyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 XERTWWFWTYYSOP-UHFFFAOYSA-N 0.000 abstract 1
• JTWGFKHCAPESJY-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-(furan-2-yl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC(C=3OC=CC=3)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 JTWGFKHCAPESJY-UHFFFAOYSA-N 0.000 abstract 1
• VVEUZPPLNHZUCN-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-(prop-2-enoxymethyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC(COCC=C)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 VVEUZPPLNHZUCN-UHFFFAOYSA-N 0.000 abstract 1
• PYSFKPLKDUHZAJ-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-(propoxymethyl)carbazol-4-yl]oxyacetic acid Chemical compound C=1C(COCCC)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 PYSFKPLKDUHZAJ-UHFFFAOYSA-N 0.000 abstract 1
• LUMYPAZSFDGHFI-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-[tri(propan-2-yl)silyloxymethyl]carbazol-4-yl]oxyacetic acid Chemical compound C=1C(CO[Si](C(C)C)(C(C)C)C(C)C)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 LUMYPAZSFDGHFI-UHFFFAOYSA-N 0.000 abstract 1
• APSSLGLEOLPZAI-UHFFFAOYSA-N 9-benzyl-5-[2-(methanesulfonamido)ethoxy]-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C12=CC(OC)=CC(OCCNS(C)(=O)=O)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 APSSLGLEOLPZAI-UHFFFAOYSA-N 0.000 abstract 1
• AELSAUYZEFGGJU-UHFFFAOYSA-N 9-benzyl-5-[2-(methanesulfonamido)ethoxy]-7-methoxycarbazole-4-carboxamide Chemical compound C=1C(OC)=CC(OCCNS(C)(=O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 AELSAUYZEFGGJU-UHFFFAOYSA-N 0.000 abstract 1
• KDHXHMORUAHVQC-UHFFFAOYSA-M lithium;2-[9-benzyl-5-carbamoyl-2-[tri(propan-2-yl)silyloxymethyl]carbazol-4-yl]oxyacetate Chemical compound [Li+].C=1C(CO[Si](C(C)C)(C(C)C)C(C)C)=CC(OCC([O-])=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 KDHXHMORUAHVQC-UHFFFAOYSA-M 0.000 abstract 1
• DDIVPTBAYACPPE-UHFFFAOYSA-M sodium;2-[(9-benzyl-5-carbamoyl-2-methoxy-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetate Chemical compound [Na+].C12=CC(OC)=CC(OCC([O-])=O)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 DDIVPTBAYACPPE-UHFFFAOYSA-M 0.000 abstract 1
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• 239000000047 product Substances 0.000 description 41
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• 239000000243 solution Substances 0.000 description 39
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• 239000002585 base Substances 0.000 description 29
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• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 27
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• 238000005481 NMR spectroscopy Methods 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 description 27
• 238000000921 elemental analysis Methods 0.000 description 27
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
• 239000012267 brine Substances 0.000 description 24
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
• 150000003254 radicals Chemical class 0.000 description 23
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• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000010410 layer Substances 0.000 description 21
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• 229910052938 sodium sulfate Inorganic materials 0.000 description 21
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
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• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 14
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
• 239000003054 catalyst Substances 0.000 description 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
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• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
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• 238000005804 alkylation reaction Methods 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 10
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
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• 239000002244 precipitate Substances 0.000 description 10
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• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 9
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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• 230000029936 alkylation Effects 0.000 description 8
• 238000004440 column chromatography Methods 0.000 description 8
• YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 8
• XCBKEVAXNVDHMT-UHFFFAOYSA-N methyl 5-hydroxy-9H-carbazole-4-carboxylate Chemical compound OC1=CC=CC=2NC3=CC=CC(=C3C1=2)C(=O)OC XCBKEVAXNVDHMT-UHFFFAOYSA-N 0.000 description 8
• 239000002480 mineral oil Substances 0.000 description 8
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• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 7
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 7
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• 125000004429 atom Chemical group 0.000 description 7
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• 238000010992 reflux Methods 0.000 description 7
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• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• 125000002877 alkyl aryl group Chemical group 0.000 description 6
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• 229910021529 ammonia Inorganic materials 0.000 description 6
• YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 6
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• YUWPKYJCYRFBJT-UHFFFAOYSA-N methyl 2-bromo-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1Br YUWPKYJCYRFBJT-UHFFFAOYSA-N 0.000 description 6
• NIXWZYZFLFEHMB-UHFFFAOYSA-N methyl 3-amino-2-bromobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1Br NIXWZYZFLFEHMB-UHFFFAOYSA-N 0.000 description 6
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• XOGIKWSCTIFLGT-UHFFFAOYSA-N methyl 9h-carbazole-1-carboxylate Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(=O)OC XOGIKWSCTIFLGT-UHFFFAOYSA-N 0.000 description 2
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• 229910000105 potassium hydride Inorganic materials 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 125000004742 propyloxycarbonyl group Chemical group 0.000 description 2
• 230000002829 reductive effect Effects 0.000 description 2
• 125000006413 ring segment Chemical group 0.000 description 2
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• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
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• 238000003756 stirring Methods 0.000 description 2
• 125000000547 substituted alkyl group Chemical group 0.000 description 2
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• 238000004809 thin layer chromatography Methods 0.000 description 2
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• 230000008025 crystallization Effects 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 230000017858 demethylation Effects 0.000 description 1
• 238000010520 demethylation reaction Methods 0.000 description 1
• 238000000151 deposition Methods 0.000 description 1
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• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
• 239000012973 diazabicyclooctane Substances 0.000 description 1
• 150000001993 dienes Chemical class 0.000 description 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• 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 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 238000001456 electron microprobe Auger spectroscopy Methods 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 230000004761 fibrosis Effects 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 230000009931 harmful effect Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 125000005980 hexynyl group Chemical group 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 210000001503 joint Anatomy 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229910003002 lithium salt Inorganic materials 0.000 description 1
• HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
• URPRVBIULYUOOY-UHFFFAOYSA-N lithium;phenylmethoxymethylbenzene Chemical compound [Li].C=1C=CC=CC=1COCC1=CC=CC=C1 URPRVBIULYUOOY-UHFFFAOYSA-N 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• QAGFBWORHHSDLU-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-2-methylcarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C)=CC=2N1CC1=CC=CC=C1 QAGFBWORHHSDLU-UHFFFAOYSA-N 0.000 description 1
• YSCQNQWTIHYXKX-UHFFFAOYSA-N methyl 2-[(5-carbamoyl-1-chloro-9h-carbazol-4-yl)oxy]acetate Chemical compound N1C2=CC=CC(C(N)=O)=C2C2=C1C(Cl)=CC=C2OCC(=O)OC YSCQNQWTIHYXKX-UHFFFAOYSA-N 0.000 description 1
• FKLVMNXPUVLIGA-UHFFFAOYSA-N methyl 2-[2-(5-cyanopentyl)-5-(hydrazinecarbonyl)-9-tridecylcarbazol-3-yl]oxyacetate Chemical compound C1=CC=C2N(CCCCCCCCCCCCC)C3=CC(CCCCCC#N)=C(OCC(=O)OC)C=C3C2=C1C(=O)NN FKLVMNXPUVLIGA-UHFFFAOYSA-N 0.000 description 1
• AKEHBKSQLIURAR-UHFFFAOYSA-N methyl 2-[[2-(5-cyanopentyl)-5-(hydrazinecarbonyl)-9-tridecyl-5,6,7,8-tetrahydrocarbazol-3-yl]oxy]acetate Chemical compound C12=CC(OCC(=O)OC)=C(CCCCCC#N)C=C2N(CCCCCCCCCCCCC)C2=C1C(C(=O)NN)CCC2 AKEHBKSQLIURAR-UHFFFAOYSA-N 0.000 description 1
• WBFLFLNAZDXPFD-UHFFFAOYSA-N methyl 2-[[5-carbamoyl-2-(5-cyanopentyl)-8-methyl-9-tridecyl-5,6,7,8-tetrahydrocarbazol-3-yl]oxy]acetate Chemical compound C12=CC(OCC(=O)OC)=C(CCCCCC#N)C=C2N(CCCCCCCCCCCCC)C2=C1C(C(N)=O)CCC2C WBFLFLNAZDXPFD-UHFFFAOYSA-N 0.000 description 1
• IIDQEGZLUKSTFK-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-6-pentylcyclohexen-1-yl)amino]benzoate Chemical compound CCCCCC1CCC(=O)C=C1NC1=CC=CC(C(=O)OC)=C1Br IIDQEGZLUKSTFK-UHFFFAOYSA-N 0.000 description 1
• QNYCSKNYBBBYLA-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-6-phenylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C=2C=CC=CC=2)=C1Br QNYCSKNYBBBYLA-UHFFFAOYSA-N 0.000 description 1
• OQOMZSWKTCSKJV-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-6-propan-2-ylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C(C)C)=C1Br OQOMZSWKTCSKJV-UHFFFAOYSA-N 0.000 description 1
• ZBSOAAIJVOCBEH-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CCCC(=O)C=2)=C1Br ZBSOAAIJVOCBEH-UHFFFAOYSA-N 0.000 description 1
• MJIGGHIPDLCHQF-UHFFFAOYSA-N methyl 2-bromo-3-[(6-ethyl-3-oxocyclohexen-1-yl)amino]benzoate Chemical compound CCC1CCC(=O)C=C1NC1=CC=CC(C(=O)OC)=C1Br MJIGGHIPDLCHQF-UHFFFAOYSA-N 0.000 description 1
• BIVYYSRZSUOCKD-UHFFFAOYSA-N methyl 2-bromo-3-[(6-methyl-3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C)=C1Br BIVYYSRZSUOCKD-UHFFFAOYSA-N 0.000 description 1
• AQCLHQGGCXNIQX-UHFFFAOYSA-N methyl 2-bromo-3-[[6-(4-chlorophenyl)-3-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C=2C=CC(Cl)=CC=2)=C1Br AQCLHQGGCXNIQX-UHFFFAOYSA-N 0.000 description 1
• CAIZYTOMOSPKEK-UHFFFAOYSA-N methyl 2-chloro-3-[(3-oxo-6-pentylcyclohexen-1-yl)amino]benzoate Chemical compound CCCCCC1CCC(=O)C=C1NC1=CC=CC(C(=O)OC)=C1Cl CAIZYTOMOSPKEK-UHFFFAOYSA-N 0.000 description 1
• GWDCUGSQAXIHGO-UHFFFAOYSA-N methyl 2-chloro-3-[(3-oxo-6-phenylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C=2C=CC=CC=2)=C1Cl GWDCUGSQAXIHGO-UHFFFAOYSA-N 0.000 description 1
• ZVNWTJUQMDGTKR-UHFFFAOYSA-N methyl 2-chloro-3-[(3-oxo-6-propan-2-ylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C(C)C)=C1Cl ZVNWTJUQMDGTKR-UHFFFAOYSA-N 0.000 description 1
• PHPULYFYWVNCCX-UHFFFAOYSA-N methyl 2-chloro-3-[(3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CCCC(=O)C=2)=C1Cl PHPULYFYWVNCCX-UHFFFAOYSA-N 0.000 description 1
• UUZDAMKDUVPPKN-UHFFFAOYSA-N methyl 2-chloro-3-[(6-ethyl-3-oxocyclohexen-1-yl)amino]benzoate Chemical compound CCC1CCC(=O)C=C1NC1=CC=CC(C(=O)OC)=C1Cl UUZDAMKDUVPPKN-UHFFFAOYSA-N 0.000 description 1
• SMUIHKVOHRKVBU-UHFFFAOYSA-N methyl 2-chloro-3-[(6-methyl-3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C)=C1Cl SMUIHKVOHRKVBU-UHFFFAOYSA-N 0.000 description 1
• QFNAVZQVWSRVQK-UHFFFAOYSA-N methyl 2-chloro-3-[[6-(4-chlorophenyl)-3-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C=2C=CC(Cl)=CC=2)=C1Cl QFNAVZQVWSRVQK-UHFFFAOYSA-N 0.000 description 1
• PICIZTABJVQXTL-UHFFFAOYSA-N methyl 2-iodo-3-[(3-oxo-6-phenylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C=2C=CC=CC=2)=C1I PICIZTABJVQXTL-UHFFFAOYSA-N 0.000 description 1
• ZNLUEVZXOTZTAN-UHFFFAOYSA-N methyl 2-iodo-3-[(3-oxo-6-propan-2-ylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C(C)C)=C1I ZNLUEVZXOTZTAN-UHFFFAOYSA-N 0.000 description 1
• KVOGSRZMJKFPSI-UHFFFAOYSA-N methyl 2-iodo-3-[(3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CCCC(=O)C=2)=C1I KVOGSRZMJKFPSI-UHFFFAOYSA-N 0.000 description 1
• ISLFKTYJFBQGJB-UHFFFAOYSA-N methyl 2-iodo-3-[(6-methyl-3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C)=C1I ISLFKTYJFBQGJB-UHFFFAOYSA-N 0.000 description 1
• TUSCIAVREPGUQH-UHFFFAOYSA-N methyl 3-[(6-ethyl-3-oxocyclohexen-1-yl)amino]-2-iodobenzoate Chemical compound CCC1CCC(=O)C=C1NC1=CC=CC(C(=O)OC)=C1I TUSCIAVREPGUQH-UHFFFAOYSA-N 0.000 description 1
• HXTCCWWGBQJQGH-UHFFFAOYSA-N methyl 3-[[6-(4-chlorophenyl)-3-oxocyclohexen-1-yl]amino]-2-iodobenzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCC(=O)C=2)C=2C=CC(Cl)=CC=2)=C1I HXTCCWWGBQJQGH-UHFFFAOYSA-N 0.000 description 1
• BWRIDGZHHUOJEQ-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-9-(naphthalen-1-ylmethyl)carbazole-4-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC(C)=CC(O)=C2C2=C1C=CC=C2C(=O)OC BWRIDGZHHUOJEQ-UHFFFAOYSA-N 0.000 description 1
• TYKKSFREWKGVNN-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-9-(naphthalen-2-ylmethyl)carbazole-4-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1CN1C2=CC(C)=CC(O)=C2C2=C1C=CC=C2C(=O)OC TYKKSFREWKGVNN-UHFFFAOYSA-N 0.000 description 1
• WNARMMSATLZTQB-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-9-[(2-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 WNARMMSATLZTQB-UHFFFAOYSA-N 0.000 description 1
• VBTWSQCWZCSBLD-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-9-[(3-phenoxyphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 VBTWSQCWZCSBLD-UHFFFAOYSA-N 0.000 description 1
• CJDSSJDMPFIPLZ-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-9-[(3-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 CJDSSJDMPFIPLZ-UHFFFAOYSA-N 0.000 description 1
• NCPVELMTGCAVPX-UHFFFAOYSA-N methyl 5-hydroxy-7-pentyl-9-[(2-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1C1=CC=CC=C1 NCPVELMTGCAVPX-UHFFFAOYSA-N 0.000 description 1
• ZAIFKKALJCWCJB-UHFFFAOYSA-N methyl 5-hydroxy-7-pentyl-9-[(3-phenoxyphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC(C=1)=CC=CC=1OC1=CC=CC=C1 ZAIFKKALJCWCJB-UHFFFAOYSA-N 0.000 description 1
• DNLBSRWWGYHVIB-UHFFFAOYSA-N methyl 5-hydroxy-7-pentyl-9-[(3-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC(C=1)=CC=CC=1C1=CC=CC=C1 DNLBSRWWGYHVIB-UHFFFAOYSA-N 0.000 description 1
• PMPAXQSDKLZXFG-UHFFFAOYSA-N methyl 5-hydroxy-7-pentyl-9-[[2-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1C(F)(F)F PMPAXQSDKLZXFG-UHFFFAOYSA-N 0.000 description 1
• LAZPHMJLQHJMGY-UHFFFAOYSA-N methyl 5-hydroxy-7-pentyl-9-[[3-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(C(F)(F)F)=C1 LAZPHMJLQHJMGY-UHFFFAOYSA-N 0.000 description 1
• BIROIIUZMODSOA-UHFFFAOYSA-N methyl 5-hydroxy-7-phenyl-9-[(2-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 BIROIIUZMODSOA-UHFFFAOYSA-N 0.000 description 1
• ZPDPPYHZGORRGL-UHFFFAOYSA-N methyl 5-hydroxy-7-phenyl-9-[(3-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 ZPDPPYHZGORRGL-UHFFFAOYSA-N 0.000 description 1
• QVJGZQOROSAPFJ-UHFFFAOYSA-N methyl 5-hydroxy-7-propan-2-yl-9-[[2-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F QVJGZQOROSAPFJ-UHFFFAOYSA-N 0.000 description 1
• QDCBKOAJWXORQI-UHFFFAOYSA-N methyl 5-hydroxy-7-propan-2-yl-9-[[3-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 QDCBKOAJWXORQI-UHFFFAOYSA-N 0.000 description 1
• IVWZHZWCQFOMOG-UHFFFAOYSA-N methyl 5-hydroxy-9-(naphthalen-1-ylmethyl)-7-phenylcarbazole-4-carboxylate Chemical compound C=1C(O)=C2C=3C(C(=O)OC)=CC=CC=3N(CC=3C4=CC=CC=C4C=CC=3)C2=CC=1C1=CC=CC=C1 IVWZHZWCQFOMOG-UHFFFAOYSA-N 0.000 description 1
• PMSZGPAYZCNLHJ-UHFFFAOYSA-N methyl 5-hydroxy-9-(naphthalen-1-ylmethyl)-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC(C(C)C)=CC(O)=C2C2=C1C=CC=C2C(=O)OC PMSZGPAYZCNLHJ-UHFFFAOYSA-N 0.000 description 1
• DEJNWOYTOSFGQM-UHFFFAOYSA-N methyl 5-hydroxy-9-(naphthalen-1-ylmethyl)carbazole-4-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC=CC(O)=C2C2=C1C=CC=C2C(=O)OC DEJNWOYTOSFGQM-UHFFFAOYSA-N 0.000 description 1
• BHLDKMTWLMNBPO-UHFFFAOYSA-N methyl 5-hydroxy-9-(naphthalen-2-ylmethyl)-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1CN1C2=CC(C(C)C)=CC(O)=C2C2=C1C=CC=C2C(=O)OC BHLDKMTWLMNBPO-UHFFFAOYSA-N 0.000 description 1
• RYHBIFNRIGPXKU-UHFFFAOYSA-N methyl 5-hydroxy-9-(naphthalen-2-ylmethyl)carbazole-4-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1CN1C2=CC=CC(O)=C2C2=C1C=CC=C2C(=O)OC RYHBIFNRIGPXKU-UHFFFAOYSA-N 0.000 description 1
• BKLXZBXIWXJYQS-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-methylphenyl)methyl]-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1C BKLXZBXIWXJYQS-UHFFFAOYSA-N 0.000 description 1
• VILYRRGQIDWDNR-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-methylphenyl)methyl]-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C VILYRRGQIDWDNR-UHFFFAOYSA-N 0.000 description 1
• TXIMAAQNACABIM-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-methylphenyl)methyl]-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C TXIMAAQNACABIM-UHFFFAOYSA-N 0.000 description 1
• ARDQVFMQRBQSHU-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-phenoxyphenyl)methyl]-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1OC1=CC=CC=C1 ARDQVFMQRBQSHU-UHFFFAOYSA-N 0.000 description 1
• GWOZTGOJWLACTM-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-phenoxyphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1OC1=CC=CC=C1 GWOZTGOJWLACTM-UHFFFAOYSA-N 0.000 description 1
• BAROVEUHVFXUSD-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-phenylphenyl)methyl]-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 BAROVEUHVFXUSD-UHFFFAOYSA-N 0.000 description 1
• PSMRXSIQLZUHLF-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 PSMRXSIQLZUHLF-UHFFFAOYSA-N 0.000 description 1
• PUTTVUWZQQYPKP-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-methylphenyl)methyl]-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(C)=C1 PUTTVUWZQQYPKP-UHFFFAOYSA-N 0.000 description 1
• JVQAUARIWKBRKM-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-methylphenyl)methyl]-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 JVQAUARIWKBRKM-UHFFFAOYSA-N 0.000 description 1
• JTKWNYITOQIFMU-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-phenoxyphenyl)methyl]-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 JTKWNYITOQIFMU-UHFFFAOYSA-N 0.000 description 1
• SQWPEVLBTUHUNC-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-phenylphenyl)methyl]-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 SQWPEVLBTUHUNC-UHFFFAOYSA-N 0.000 description 1
• WWVYPNHAZMEWHO-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 WWVYPNHAZMEWHO-UHFFFAOYSA-N 0.000 description 1
• FOXVVTFPAJNFNP-UHFFFAOYSA-N methyl 5-oxo-7-pentyl-9-[(2-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1OC1=CC=CC=C1 FOXVVTFPAJNFNP-UHFFFAOYSA-N 0.000 description 1
• SXIBAEQIQCDVAV-UHFFFAOYSA-N methyl 5-oxo-7-pentyl-9-[(2-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1C1=CC=CC=C1 SXIBAEQIQCDVAV-UHFFFAOYSA-N 0.000 description 1
• KLQQPXXDZJMDDE-UHFFFAOYSA-N methyl 5-oxo-7-pentyl-9-[(3-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC(C=1)=CC=CC=1OC1=CC=CC=C1 KLQQPXXDZJMDDE-UHFFFAOYSA-N 0.000 description 1
• QFGVNOFNVDKEIZ-UHFFFAOYSA-N methyl 5-oxo-7-pentyl-9-[(3-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC(C=1)=CC=CC=1C1=CC=CC=C1 QFGVNOFNVDKEIZ-UHFFFAOYSA-N 0.000 description 1
• UQJGZSVTABFYIV-UHFFFAOYSA-N methyl 5-oxo-7-phenyl-9-[(2-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 UQJGZSVTABFYIV-UHFFFAOYSA-N 0.000 description 1
• RXLHOUOYYXPVPJ-UHFFFAOYSA-N methyl 5-oxo-7-phenyl-9-[(3-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 RXLHOUOYYXPVPJ-UHFFFAOYSA-N 0.000 description 1
• AVVJORZFJOQDJL-UHFFFAOYSA-N methyl 5-oxo-7-phenyl-9-[[2-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F AVVJORZFJOQDJL-UHFFFAOYSA-N 0.000 description 1
• YTXBALCCCZYKLW-UHFFFAOYSA-N methyl 5-oxo-7-phenyl-9-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 YTXBALCCCZYKLW-UHFFFAOYSA-N 0.000 description 1
• PWYSQXQKLZRXCF-UHFFFAOYSA-N methyl 5-oxo-7-propan-2-yl-9-[[2-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F PWYSQXQKLZRXCF-UHFFFAOYSA-N 0.000 description 1
• FXQTUISBRQSBAR-UHFFFAOYSA-N methyl 5-oxo-7-propan-2-yl-9-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 FXQTUISBRQSBAR-UHFFFAOYSA-N 0.000 description 1
• JHGJZUIUYVNWPP-UHFFFAOYSA-N methyl 5-oxo-9-[(2-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1OC1=CC=CC=C1 JHGJZUIUYVNWPP-UHFFFAOYSA-N 0.000 description 1
• REXZMTKRNXBKDC-UHFFFAOYSA-N methyl 5-oxo-9-[(2-phenoxyphenyl)methyl]-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1OC1=CC=CC=C1 REXZMTKRNXBKDC-UHFFFAOYSA-N 0.000 description 1
• CBNFKFOWMMBIAJ-UHFFFAOYSA-N methyl 5-oxo-9-[(2-phenoxyphenyl)methyl]-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1OC1=CC=CC=C1 CBNFKFOWMMBIAJ-UHFFFAOYSA-N 0.000 description 1
• KCMMNBOJQLJLLU-UHFFFAOYSA-N methyl 5-oxo-9-[(2-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 KCMMNBOJQLJLLU-UHFFFAOYSA-N 0.000 description 1
• DPKZXCMYWMAJSW-UHFFFAOYSA-N methyl 5-oxo-9-[(2-phenylphenyl)methyl]-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 DPKZXCMYWMAJSW-UHFFFAOYSA-N 0.000 description 1
• RCRXNQNAKYCNKR-UHFFFAOYSA-N methyl 5-oxo-9-[(3-phenoxyphenyl)methyl]-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 RCRXNQNAKYCNKR-UHFFFAOYSA-N 0.000 description 1
• OYRFYCXKAYMDEZ-UHFFFAOYSA-N methyl 5-oxo-9-[(3-phenoxyphenyl)methyl]-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 OYRFYCXKAYMDEZ-UHFFFAOYSA-N 0.000 description 1
• HQYYBLQNPNXSOL-UHFFFAOYSA-N methyl 5-oxo-9-[(3-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 HQYYBLQNPNXSOL-UHFFFAOYSA-N 0.000 description 1
• TWHAQFPVFPWMGM-UHFFFAOYSA-N methyl 5-oxo-9-[(3-phenylphenyl)methyl]-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 TWHAQFPVFPWMGM-UHFFFAOYSA-N 0.000 description 1
• KDQDLQGPJGEREI-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-(naphthalen-1-ylmethyl)carbazole-4-carboxylate Chemical compound C=1C(O)=C2C=3C(C(=O)OC)=CC=CC=3N(CC=3C4=CC=CC=C4C=CC=3)C2=CC=1C1=CC=C(Cl)C=C1 KDQDLQGPJGEREI-UHFFFAOYSA-N 0.000 description 1
• WYFKVJJGLQFVDJ-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-(naphthalen-2-ylmethyl)carbazole-4-carboxylate Chemical compound C=1C(O)=C2C=3C(C(=O)OC)=CC=CC=3N(CC=3C=C4C=CC=CC4=CC=3)C2=CC=1C1=CC=C(Cl)C=C1 WYFKVJJGLQFVDJ-UHFFFAOYSA-N 0.000 description 1
• BRDQWMUKTCWRRN-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-[(2-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C BRDQWMUKTCWRRN-UHFFFAOYSA-N 0.000 description 1
• QSOQUYPUNRYRCY-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-[(2-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 QSOQUYPUNRYRCY-UHFFFAOYSA-N 0.000 description 1
• KKFQTDIWTCJBHI-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-[(3-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 KKFQTDIWTCJBHI-UHFFFAOYSA-N 0.000 description 1
• QJQYDZFHRKAWPJ-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-[(3-phenoxyphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 QJQYDZFHRKAWPJ-UHFFFAOYSA-N 0.000 description 1
• PMEYLPITTZJJLP-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-[(3-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 PMEYLPITTZJJLP-UHFFFAOYSA-N 0.000 description 1
• LWDOCBBHHZTEBY-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-[[2-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F LWDOCBBHHZTEBY-UHFFFAOYSA-N 0.000 description 1
• YTENVFJMALYRCR-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-hydroxy-9-[[3-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 YTENVFJMALYRCR-UHFFFAOYSA-N 0.000 description 1
• DWCDEUVYRVYCCD-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-oxo-9-[(2-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1OC1=CC=CC=C1 DWCDEUVYRVYCCD-UHFFFAOYSA-N 0.000 description 1
• CQRCPUDFTSORIJ-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-oxo-9-[(2-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 CQRCPUDFTSORIJ-UHFFFAOYSA-N 0.000 description 1
• UCWSGOXFPWHSCU-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-oxo-9-[(3-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 UCWSGOXFPWHSCU-UHFFFAOYSA-N 0.000 description 1
• BFYDMLBKHUHFKR-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-oxo-9-[(3-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 BFYDMLBKHUHFKR-UHFFFAOYSA-N 0.000 description 1
• YCRSBVYXLHLBMF-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-oxo-9-[[2-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F YCRSBVYXLHLBMF-UHFFFAOYSA-N 0.000 description 1
• FVFBQWYCUCTPBZ-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-oxo-9-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 FVFBQWYCUCTPBZ-UHFFFAOYSA-N 0.000 description 1
• FEVIKIYRZOBYGN-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-(naphthalen-1-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3N(CC=3C4=CC=CC=C4C=CC=3)C=2CC1C1=CC=C(Cl)C=C1 FEVIKIYRZOBYGN-UHFFFAOYSA-N 0.000 description 1
• PXMZLTOUFGCWCT-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-(naphthalen-2-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3N(CC=3C=C4C=CC=CC4=CC=3)C=2CC1C1=CC=C(Cl)C=C1 PXMZLTOUFGCWCT-UHFFFAOYSA-N 0.000 description 1
• AOJCBUZYHDEYBT-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(2-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl AOJCBUZYHDEYBT-UHFFFAOYSA-N 0.000 description 1
• JHYYVUIBNMLAQC-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(2-chlorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl JHYYVUIBNMLAQC-UHFFFAOYSA-N 0.000 description 1
• LXKCNGUPPYVHMQ-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(2-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N LXKCNGUPPYVHMQ-UHFFFAOYSA-N 0.000 description 1
• VUIXUKPHNUGIAO-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(2-cyanophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N VUIXUKPHNUGIAO-UHFFFAOYSA-N 0.000 description 1
• GHYFCYPIVXJKFD-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(2-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F GHYFCYPIVXJKFD-UHFFFAOYSA-N 0.000 description 1
• BPIVKFBRDFTGOR-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(2-fluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F BPIVKFBRDFTGOR-UHFFFAOYSA-N 0.000 description 1
• IBAFTWHEODEKAV-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(2-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C IBAFTWHEODEKAV-UHFFFAOYSA-N 0.000 description 1
• BKZYLQOCKFACHH-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(3-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 BKZYLQOCKFACHH-UHFFFAOYSA-N 0.000 description 1
• DVLMLPBMTMVPHB-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(3-chlorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 DVLMLPBMTMVPHB-UHFFFAOYSA-N 0.000 description 1
• ZQAWHLHHNOLJDU-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(3-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 ZQAWHLHHNOLJDU-UHFFFAOYSA-N 0.000 description 1
• MZKROLJRWOGCGO-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(3-cyanophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 MZKROLJRWOGCGO-UHFFFAOYSA-N 0.000 description 1
• OROMPALSRHVWFW-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(3-fluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 OROMPALSRHVWFW-UHFFFAOYSA-N 0.000 description 1
• CLZJCRBVUHZRGN-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-9-[(3-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 CLZJCRBVUHZRGN-UHFFFAOYSA-N 0.000 description 1
• LWFNWSBIVNFSBM-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-(naphthalen-1-ylmethyl)carbazole-4-carboxylate Chemical compound C12=CC=CC(C(=O)OC)=C2C2=C(O)C=C(CC)C=C2N1CC1=CC=CC2=CC=CC=C12 LWFNWSBIVNFSBM-UHFFFAOYSA-N 0.000 description 1
• VKIBVYWOPWQJIM-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-(naphthalen-2-ylmethyl)carbazole-4-carboxylate Chemical compound C12=CC=CC(C(=O)OC)=C2C2=C(O)C=C(CC)C=C2N1CC1=CC=C(C=CC=C2)C2=C1 VKIBVYWOPWQJIM-UHFFFAOYSA-N 0.000 description 1
• CYUGBWAPIOENFL-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-[(2-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1C CYUGBWAPIOENFL-UHFFFAOYSA-N 0.000 description 1
• XKTXDOLCNYICQT-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-[(2-phenoxyphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1OC1=CC=CC=C1 XKTXDOLCNYICQT-UHFFFAOYSA-N 0.000 description 1
• IOFQJHWSROCYOR-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-[(2-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1C1=CC=CC=C1 IOFQJHWSROCYOR-UHFFFAOYSA-N 0.000 description 1
• GXOAGYJXEHVXBR-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-[(3-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(C)=C1 GXOAGYJXEHVXBR-UHFFFAOYSA-N 0.000 description 1
• SLPBBXLRASSUAK-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-[(3-phenoxyphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC(C=1)=CC=CC=1OC1=CC=CC=C1 SLPBBXLRASSUAK-UHFFFAOYSA-N 0.000 description 1
• LMRQDVUVONHDKE-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-[(3-phenylphenyl)methyl]carbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC(C=1)=CC=CC=1C1=CC=CC=C1 LMRQDVUVONHDKE-UHFFFAOYSA-N 0.000 description 1
• PALYOZQRXVEMFD-UHFFFAOYSA-N methyl 7-ethyl-5-hydroxy-9-[[2-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1C(F)(F)F PALYOZQRXVEMFD-UHFFFAOYSA-N 0.000 description 1
• NVYLMLZNKMPXOK-UHFFFAOYSA-N methyl 7-ethyl-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound N1C2=CC=CC(C(=O)OC)=C2C2=C1CC(CC)CC2=O NVYLMLZNKMPXOK-UHFFFAOYSA-N 0.000 description 1
• VSZMXUZSFUDTOG-UHFFFAOYSA-N methyl 7-ethyl-5-oxo-9-[(2-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1OC1=CC=CC=C1 VSZMXUZSFUDTOG-UHFFFAOYSA-N 0.000 description 1
• DWANOEQCEARLCQ-UHFFFAOYSA-N methyl 7-ethyl-5-oxo-9-[(2-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1C1=CC=CC=C1 DWANOEQCEARLCQ-UHFFFAOYSA-N 0.000 description 1
• JCEBGJZBEKMENZ-UHFFFAOYSA-N methyl 7-ethyl-5-oxo-9-[(3-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC(C=1)=CC=CC=1OC1=CC=CC=C1 JCEBGJZBEKMENZ-UHFFFAOYSA-N 0.000 description 1
• MULHHXUEHCDCSU-UHFFFAOYSA-N methyl 7-ethyl-5-oxo-9-[(3-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC(C=1)=CC=CC=1C1=CC=CC=C1 MULHHXUEHCDCSU-UHFFFAOYSA-N 0.000 description 1
• MEYIYHLNZHLRDN-UHFFFAOYSA-N methyl 7-ethyl-5-oxo-9-[[2-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1C(F)(F)F MEYIYHLNZHLRDN-UHFFFAOYSA-N 0.000 description 1
• VEAUWVOCXAORDR-UHFFFAOYSA-N methyl 7-ethyl-5-oxo-9-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(C(F)(F)F)=C1 VEAUWVOCXAORDR-UHFFFAOYSA-N 0.000 description 1
• SYQZOOSGHPXWMZ-UHFFFAOYSA-N methyl 7-ethyl-9-(naphthalen-1-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=CC=C2C(CN3C4=CC=CC(=C4C4=C3CC(CC4=O)CC)C(=O)OC)=CC=CC2=C1 SYQZOOSGHPXWMZ-UHFFFAOYSA-N 0.000 description 1
• FGYXQHPKIYQBMU-UHFFFAOYSA-N methyl 7-ethyl-9-(naphthalen-2-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=CC=CC2=CC(CN3C4=CC=CC(=C4C4=C3CC(CC4=O)CC)C(=O)OC)=CC=C21 FGYXQHPKIYQBMU-UHFFFAOYSA-N 0.000 description 1
• JKYNWMKMMFOZNZ-UHFFFAOYSA-N methyl 7-ethyl-9-[(2-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1F JKYNWMKMMFOZNZ-UHFFFAOYSA-N 0.000 description 1
• ZVBQCEMXZAUNJQ-UHFFFAOYSA-N methyl 7-ethyl-9-[(2-fluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1F ZVBQCEMXZAUNJQ-UHFFFAOYSA-N 0.000 description 1
• OPETZBUKRSJNND-UHFFFAOYSA-N methyl 7-ethyl-9-[(2-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1C OPETZBUKRSJNND-UHFFFAOYSA-N 0.000 description 1
• OOWGVRQIKGCVES-UHFFFAOYSA-N methyl 7-ethyl-9-[(3-fluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(F)=C1 OOWGVRQIKGCVES-UHFFFAOYSA-N 0.000 description 1
• TWYMXFLBSICZJC-UHFFFAOYSA-N methyl 7-ethyl-9-[(3-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(C)=C1 TWYMXFLBSICZJC-UHFFFAOYSA-N 0.000 description 1
• XMVHZUCQRQLDDD-UHFFFAOYSA-N methyl 7-methyl-5-oxo-9-[(2-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1OC1=CC=CC=C1 XMVHZUCQRQLDDD-UHFFFAOYSA-N 0.000 description 1
• IWPYBBHAZLBUSW-UHFFFAOYSA-N methyl 7-methyl-5-oxo-9-[(2-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1 IWPYBBHAZLBUSW-UHFFFAOYSA-N 0.000 description 1
• YCRZCGBLFWXBQA-UHFFFAOYSA-N methyl 7-methyl-5-oxo-9-[(3-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 YCRZCGBLFWXBQA-UHFFFAOYSA-N 0.000 description 1
• WNRXCCGCAMITPX-UHFFFAOYSA-N methyl 7-methyl-5-oxo-9-[(3-phenylphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 WNRXCCGCAMITPX-UHFFFAOYSA-N 0.000 description 1
• SCHITSNANZIVNN-UHFFFAOYSA-N methyl 7-methyl-5-oxo-9-[[2-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F SCHITSNANZIVNN-UHFFFAOYSA-N 0.000 description 1
• DVPZEBVULVNFDT-UHFFFAOYSA-N methyl 7-methyl-5-oxo-9-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 DVPZEBVULVNFDT-UHFFFAOYSA-N 0.000 description 1
• DJKOFSVYGZGISK-UHFFFAOYSA-N methyl 7-methyl-9-(naphthalen-1-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1C(C)CC(=O)C2=C1N(CC=1C3=CC=CC=C3C=CC=1)C1=C2C(C(=O)OC)=CC=C1 DJKOFSVYGZGISK-UHFFFAOYSA-N 0.000 description 1
• UHTQVCCKTUOPRU-UHFFFAOYSA-N methyl 7-methyl-9-(naphthalen-2-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1C(C)CC(=O)C2=C1N(CC=1C=C3C=CC=CC3=CC=1)C1=C2C(C(=O)OC)=CC=C1 UHTQVCCKTUOPRU-UHFFFAOYSA-N 0.000 description 1
• HZLCOQKRNRZMBL-UHFFFAOYSA-N methyl 9-(naphthalen-1-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1CCC(=O)C2=C1N(CC=1C3=CC=CC=C3C=CC=1)C1=C2C(C(=O)OC)=CC=C1 HZLCOQKRNRZMBL-UHFFFAOYSA-N 0.000 description 1
• TTZAYBRCANGWHR-UHFFFAOYSA-N methyl 9-(naphthalen-1-ylmethyl)-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=CC=C2C(CN3C4=CC=CC(=C4C4=C3CC(CC4=O)CCCCC)C(=O)OC)=CC=CC2=C1 TTZAYBRCANGWHR-UHFFFAOYSA-N 0.000 description 1
• HGFPHIVEBBIAPM-UHFFFAOYSA-N methyl 9-(naphthalen-1-ylmethyl)-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3N(CC=3C4=CC=CC=C4C=CC=3)C=2CC1C1=CC=CC=C1 HGFPHIVEBBIAPM-UHFFFAOYSA-N 0.000 description 1
• ZDADAKMWNVYACX-UHFFFAOYSA-N methyl 9-(naphthalen-1-ylmethyl)-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1C(C(C)C)CC(=O)C2=C1N(CC=1C3=CC=CC=C3C=CC=1)C1=C2C(C(=O)OC)=CC=C1 ZDADAKMWNVYACX-UHFFFAOYSA-N 0.000 description 1
• JETPAGJJNUZVNO-UHFFFAOYSA-N methyl 9-(naphthalen-2-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1CCC(=O)C2=C1N(CC=1C=C3C=CC=CC3=CC=1)C1=C2C(C(=O)OC)=CC=C1 JETPAGJJNUZVNO-UHFFFAOYSA-N 0.000 description 1
• QGHYKWOXQFLGGA-UHFFFAOYSA-N methyl 9-(naphthalen-2-ylmethyl)-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=CC=CC2=CC(CN3C4=CC=CC(=C4C4=C3CC(CC4=O)CCCCC)C(=O)OC)=CC=C21 QGHYKWOXQFLGGA-UHFFFAOYSA-N 0.000 description 1
• JHGDEPWIDOCUCI-UHFFFAOYSA-N methyl 9-(naphthalen-2-ylmethyl)-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3N(CC=3C=C4C=CC=CC4=CC=3)C=2CC1C1=CC=CC=C1 JHGDEPWIDOCUCI-UHFFFAOYSA-N 0.000 description 1
• JQLOSOXHENUUME-UHFFFAOYSA-N methyl 9-(naphthalen-2-ylmethyl)-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1C(C(C)C)CC(=O)C2=C1N(CC=1C=C3C=CC=CC3=CC=1)C1=C2C(C(=O)OC)=CC=C1 JQLOSOXHENUUME-UHFFFAOYSA-N 0.000 description 1
• XXBMPLCVWZRECL-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 XXBMPLCVWZRECL-UHFFFAOYSA-N 0.000 description 1
• VIFZPKQCCLGOJG-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1CC1=CC=CC=C1 VIFZPKQCCLGOJG-UHFFFAOYSA-N 0.000 description 1
• FLUAEJOKWHOXMA-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 FLUAEJOKWHOXMA-UHFFFAOYSA-N 0.000 description 1
• WMZXVSWHONSJSZ-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 WMZXVSWHONSJSZ-UHFFFAOYSA-N 0.000 description 1
• RMDLRBVVUSFDPK-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 RMDLRBVVUSFDPK-UHFFFAOYSA-N 0.000 description 1
• GSKCQVFTFZVUDE-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 GSKCQVFTFZVUDE-UHFFFAOYSA-N 0.000 description 1
• BDJGHEDJAUVWPN-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1CC1=CC=CC=C1 BDJGHEDJAUVWPN-UHFFFAOYSA-N 0.000 description 1
• MSZSVGTUJWCZDU-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 MSZSVGTUJWCZDU-UHFFFAOYSA-N 0.000 description 1
• CYDDOBOGARBLNX-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 CYDDOBOGARBLNX-UHFFFAOYSA-N 0.000 description 1
• RSSPWNYCSUWGFC-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-7-(4-chlorophenyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 RSSPWNYCSUWGFC-UHFFFAOYSA-N 0.000 description 1
• WECDTDPXSACTCI-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-7-(4-chlorophenyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 WECDTDPXSACTCI-UHFFFAOYSA-N 0.000 description 1
• FRBRAMJDSNNEIO-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1CC1=CC=CC=C1 FRBRAMJDSNNEIO-UHFFFAOYSA-N 0.000 description 1
• LISYGIISSSXZHY-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1CC1=CC=CC=C1 LISYGIISSSXZHY-UHFFFAOYSA-N 0.000 description 1
• WCBPXJLWHFVECU-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 WCBPXJLWHFVECU-UHFFFAOYSA-N 0.000 description 1
• GMMQXSWCNUQRGS-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br GMMQXSWCNUQRGS-UHFFFAOYSA-N 0.000 description 1
• MDCMODOTYYJJMU-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1Br MDCMODOTYYJJMU-UHFFFAOYSA-N 0.000 description 1
• IIRRHZPNHQCIAT-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br IIRRHZPNHQCIAT-UHFFFAOYSA-N 0.000 description 1
• XCVLMAPDNCWCRI-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br XCVLMAPDNCWCRI-UHFFFAOYSA-N 0.000 description 1
• GDXQSUYWZINDOY-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br GDXQSUYWZINDOY-UHFFFAOYSA-N 0.000 description 1
• NKJQKDCXUPVHAR-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br NKJQKDCXUPVHAR-UHFFFAOYSA-N 0.000 description 1
• ODNYINJWINSJFE-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1Br ODNYINJWINSJFE-UHFFFAOYSA-N 0.000 description 1
• NQZCVSUIRDORRX-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br NQZCVSUIRDORRX-UHFFFAOYSA-N 0.000 description 1
• FPAQGTZDDFZHRL-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br FPAQGTZDDFZHRL-UHFFFAOYSA-N 0.000 description 1
• KDBLLTLCNKGYON-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-7-(4-chlorophenyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br KDBLLTLCNKGYON-UHFFFAOYSA-N 0.000 description 1
• BSNXXJZSUBELJC-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-7-(4-chlorophenyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br BSNXXJZSUBELJC-UHFFFAOYSA-N 0.000 description 1
• YYEXKRZHFFAQIV-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1Br YYEXKRZHFFAQIV-UHFFFAOYSA-N 0.000 description 1
• YGAIFCVJBMUSQO-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1Br YGAIFCVJBMUSQO-UHFFFAOYSA-N 0.000 description 1
• LITPVGRIISUAOI-UHFFFAOYSA-N methyl 9-[(2-bromophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Br LITPVGRIISUAOI-UHFFFAOYSA-N 0.000 description 1
• ZIOYNYMMMMPFPO-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl ZIOYNYMMMMPFPO-UHFFFAOYSA-N 0.000 description 1
• DWRPQHHPJURXPC-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1Cl DWRPQHHPJURXPC-UHFFFAOYSA-N 0.000 description 1
• UREKJJALGJSYSG-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl UREKJJALGJSYSG-UHFFFAOYSA-N 0.000 description 1
• QVQZQXDQBITXJP-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl QVQZQXDQBITXJP-UHFFFAOYSA-N 0.000 description 1
• UBQDHYGSBRWWOT-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1Cl UBQDHYGSBRWWOT-UHFFFAOYSA-N 0.000 description 1
• UDTXRPZWGFJBAB-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl UDTXRPZWGFJBAB-UHFFFAOYSA-N 0.000 description 1
• CWLXUBUUWGEGCM-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl CWLXUBUUWGEGCM-UHFFFAOYSA-N 0.000 description 1
• FIJYJOKNSRPJHC-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1Cl FIJYJOKNSRPJHC-UHFFFAOYSA-N 0.000 description 1
• SXCPKRFTXIPQIQ-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1Cl SXCPKRFTXIPQIQ-UHFFFAOYSA-N 0.000 description 1
• XTYRUVJTPKVBGR-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl XTYRUVJTPKVBGR-UHFFFAOYSA-N 0.000 description 1
• WHCUOJJRJUDKDT-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N WHCUOJJRJUDKDT-UHFFFAOYSA-N 0.000 description 1
• OXZXBKDFMCDOLR-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1C#N OXZXBKDFMCDOLR-UHFFFAOYSA-N 0.000 description 1
• KQRNPAFQVHFQNN-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N KQRNPAFQVHFQNN-UHFFFAOYSA-N 0.000 description 1
• AZTYVYVTFQQVHK-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N AZTYVYVTFQQVHK-UHFFFAOYSA-N 0.000 description 1
• NJMWQQFNQLDAJL-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1C#N NJMWQQFNQLDAJL-UHFFFAOYSA-N 0.000 description 1
• IEMYDFTZAARTES-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N IEMYDFTZAARTES-UHFFFAOYSA-N 0.000 description 1
• MCGQWZUPTGUNDR-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N MCGQWZUPTGUNDR-UHFFFAOYSA-N 0.000 description 1
• LXOQIIMDLAORIV-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1C#N LXOQIIMDLAORIV-UHFFFAOYSA-N 0.000 description 1
• QDZUKRMTQFNRKL-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1C#N QDZUKRMTQFNRKL-UHFFFAOYSA-N 0.000 description 1
• ZAYIKFRMFDYNNA-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N ZAYIKFRMFDYNNA-UHFFFAOYSA-N 0.000 description 1
• IILBPLZGIDFGQF-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F IILBPLZGIDFGQF-UHFFFAOYSA-N 0.000 description 1
• BAPXCCKGRIRMFU-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1F BAPXCCKGRIRMFU-UHFFFAOYSA-N 0.000 description 1
• GNZXUKXQTWFWIG-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F GNZXUKXQTWFWIG-UHFFFAOYSA-N 0.000 description 1
• ZCNYCWLVXARRKO-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F ZCNYCWLVXARRKO-UHFFFAOYSA-N 0.000 description 1
• WKWBSXJKFPBXQR-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1F WKWBSXJKFPBXQR-UHFFFAOYSA-N 0.000 description 1
• AZAFNYSRXDTOCI-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F AZAFNYSRXDTOCI-UHFFFAOYSA-N 0.000 description 1
• YFCRJOFDFSGJDA-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F YFCRJOFDFSGJDA-UHFFFAOYSA-N 0.000 description 1
• DFFRDMGMIHIHHC-UHFFFAOYSA-N methyl 9-[(2-methylphenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1C DFFRDMGMIHIHHC-UHFFFAOYSA-N 0.000 description 1
• XEMGDGSPOWZXIP-UHFFFAOYSA-N methyl 9-[(2-methylphenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C XEMGDGSPOWZXIP-UHFFFAOYSA-N 0.000 description 1
• WGZKJNFGNIHODD-UHFFFAOYSA-N methyl 9-[(2-methylphenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C WGZKJNFGNIHODD-UHFFFAOYSA-N 0.000 description 1
• MBYMETRCWWQJBW-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 MBYMETRCWWQJBW-UHFFFAOYSA-N 0.000 description 1
• ZAUXFNVVRNVIMM-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC(C=1)=CC=CC=1CC1=CC=CC=C1 ZAUXFNVVRNVIMM-UHFFFAOYSA-N 0.000 description 1
• XNTROWZSUBRNGP-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 XNTROWZSUBRNGP-UHFFFAOYSA-N 0.000 description 1
• GLTQYYFHNYRQRO-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 GLTQYYFHNYRQRO-UHFFFAOYSA-N 0.000 description 1
• CODQBZMBAWOTOD-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 CODQBZMBAWOTOD-UHFFFAOYSA-N 0.000 description 1
• MPMVVYMFGQUYEH-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC(C=1)=CC=CC=1CC1=CC=CC=C1 MPMVVYMFGQUYEH-UHFFFAOYSA-N 0.000 description 1
• COCMXVJAOORSBK-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 COCMXVJAOORSBK-UHFFFAOYSA-N 0.000 description 1
• ACRWLIZIEQYDGR-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 ACRWLIZIEQYDGR-UHFFFAOYSA-N 0.000 description 1
• VKYWVPVUQUKLRR-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-7-(4-chlorophenyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 VKYWVPVUQUKLRR-UHFFFAOYSA-N 0.000 description 1
• XVLXVPRBQXAKDR-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-7-(4-chlorophenyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 XVLXVPRBQXAKDR-UHFFFAOYSA-N 0.000 description 1
• OJYSSRSWKYCEPX-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC(C=1)=CC=CC=1CC1=CC=CC=C1 OJYSSRSWKYCEPX-UHFFFAOYSA-N 0.000 description 1
• AQNXUKJPOSPOJJ-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC(C=1)=CC=CC=1CC1=CC=CC=C1 AQNXUKJPOSPOJJ-UHFFFAOYSA-N 0.000 description 1
• QJMLZTHTBJYHEC-UHFFFAOYSA-N methyl 9-[(3-benzylphenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1CC1=CC=CC=C1 QJMLZTHTBJYHEC-UHFFFAOYSA-N 0.000 description 1
• OULMNMLBLZXCTH-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 OULMNMLBLZXCTH-UHFFFAOYSA-N 0.000 description 1
• SGGFVLQZMNAKMP-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(Br)=C1 SGGFVLQZMNAKMP-UHFFFAOYSA-N 0.000 description 1
• ZUBZHPLKODTSIP-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 ZUBZHPLKODTSIP-UHFFFAOYSA-N 0.000 description 1
• KEPKHOXDWDNENQ-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 KEPKHOXDWDNENQ-UHFFFAOYSA-N 0.000 description 1
• MJJQTKWRTTYLRI-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 MJJQTKWRTTYLRI-UHFFFAOYSA-N 0.000 description 1
• YFZABYZYEONOHS-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 YFZABYZYEONOHS-UHFFFAOYSA-N 0.000 description 1
• PCNUDBODKXXBRM-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(Br)=C1 PCNUDBODKXXBRM-UHFFFAOYSA-N 0.000 description 1
• JLFPIHLTYYDAJE-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 JLFPIHLTYYDAJE-UHFFFAOYSA-N 0.000 description 1
• HBSYPROUHCGLMW-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 HBSYPROUHCGLMW-UHFFFAOYSA-N 0.000 description 1
• OYIIKSBOBWHPJE-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-7-(4-chlorophenyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 OYIIKSBOBWHPJE-UHFFFAOYSA-N 0.000 description 1
• QJZLRYQVRMPRBJ-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-7-(4-chlorophenyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 QJZLRYQVRMPRBJ-UHFFFAOYSA-N 0.000 description 1
• AOCIDWNPDLKJTH-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(Br)=C1 AOCIDWNPDLKJTH-UHFFFAOYSA-N 0.000 description 1
• ZFVFRRQMHVVTQR-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(Br)=C1 ZFVFRRQMHVVTQR-UHFFFAOYSA-N 0.000 description 1
• PMUOGQMZEMKZET-UHFFFAOYSA-N methyl 9-[(3-bromophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Br)=C1 PMUOGQMZEMKZET-UHFFFAOYSA-N 0.000 description 1
• SQEJVPSXQZWRAC-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 SQEJVPSXQZWRAC-UHFFFAOYSA-N 0.000 description 1
• NOWSCVGVVKVMHH-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(Cl)=C1 NOWSCVGVVKVMHH-UHFFFAOYSA-N 0.000 description 1
• VJSMWAMBACIAEM-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 VJSMWAMBACIAEM-UHFFFAOYSA-N 0.000 description 1
• AYSLBDSLUUWGDK-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 AYSLBDSLUUWGDK-UHFFFAOYSA-N 0.000 description 1
• RMSKZGQSHDPGNL-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 RMSKZGQSHDPGNL-UHFFFAOYSA-N 0.000 description 1
• MTRHFEFUHCLRSE-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(Cl)=C1 MTRHFEFUHCLRSE-UHFFFAOYSA-N 0.000 description 1
• XMTNCTHKYBELMQ-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 XMTNCTHKYBELMQ-UHFFFAOYSA-N 0.000 description 1
• VPPRKWDIMOJUHZ-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 VPPRKWDIMOJUHZ-UHFFFAOYSA-N 0.000 description 1
• GGZYRMABARVTOW-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(Cl)=C1 GGZYRMABARVTOW-UHFFFAOYSA-N 0.000 description 1
• PVKSKTBDWDGDRV-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(Cl)=C1 PVKSKTBDWDGDRV-UHFFFAOYSA-N 0.000 description 1
• IDQDRQMDXKBIKU-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 IDQDRQMDXKBIKU-UHFFFAOYSA-N 0.000 description 1
• UVSMNKKNJRJXSK-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 UVSMNKKNJRJXSK-UHFFFAOYSA-N 0.000 description 1
• BWMOKVYOLRDKLF-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(C#N)=C1 BWMOKVYOLRDKLF-UHFFFAOYSA-N 0.000 description 1
• VWJMBQBKKCEBEM-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 VWJMBQBKKCEBEM-UHFFFAOYSA-N 0.000 description 1
• IMIZQUDKGVRQFX-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 IMIZQUDKGVRQFX-UHFFFAOYSA-N 0.000 description 1
• DHXAXRSRKZCZIP-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(C#N)=C1 DHXAXRSRKZCZIP-UHFFFAOYSA-N 0.000 description 1
• GFFYPVDSSPVHOJ-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 GFFYPVDSSPVHOJ-UHFFFAOYSA-N 0.000 description 1
• WOHWPAQBHSLYRR-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 WOHWPAQBHSLYRR-UHFFFAOYSA-N 0.000 description 1
• VWZISZDMEFOUKV-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(C#N)=C1 VWZISZDMEFOUKV-UHFFFAOYSA-N 0.000 description 1
• RXJQCRGIWXOVMY-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(C#N)=C1 RXJQCRGIWXOVMY-UHFFFAOYSA-N 0.000 description 1
• BMEAGYJWTPTLQM-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 BMEAGYJWTPTLQM-UHFFFAOYSA-N 0.000 description 1
• IAEOZCLKDZWRDJ-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC(F)=C1 IAEOZCLKDZWRDJ-UHFFFAOYSA-N 0.000 description 1
• FLYMXKXLBIZUNW-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 FLYMXKXLBIZUNW-UHFFFAOYSA-N 0.000 description 1
• KYQCOQXFFIYBJU-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 KYQCOQXFFIYBJU-UHFFFAOYSA-N 0.000 description 1
• HJPDEABLIMCRRQ-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(F)=C1 HJPDEABLIMCRRQ-UHFFFAOYSA-N 0.000 description 1
• KQZXLTXUEDXRML-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 KQZXLTXUEDXRML-UHFFFAOYSA-N 0.000 description 1
• CUCNHTGITUZJPB-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 CUCNHTGITUZJPB-UHFFFAOYSA-N 0.000 description 1
• XGVDQCXIDAYFCF-UHFFFAOYSA-N methyl 9-[(3-methylphenyl)methyl]-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC(C)=C1 XGVDQCXIDAYFCF-UHFFFAOYSA-N 0.000 description 1
• LZCMCQAEVBLITQ-UHFFFAOYSA-N methyl 9-[(3-methylphenyl)methyl]-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 LZCMCQAEVBLITQ-UHFFFAOYSA-N 0.000 description 1
• HXNQEKJIBQJCOV-UHFFFAOYSA-N methyl 9-[(3-methylphenyl)methyl]-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 HXNQEKJIBQJCOV-UHFFFAOYSA-N 0.000 description 1
• TUFAGSKTLXPHPK-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-[4-(trifluoromethyl)phenyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(=CC=3)C(F)(F)F)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 TUFAGSKTLXPHPK-UHFFFAOYSA-N 0.000 description 1
• QKVUDZSFJQIGHW-UHFFFAOYSA-N methyl 9-benzyl-7-ethyl-5-hydroxycarbazole-4-carboxylate Chemical compound C=1C(CC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1 QKVUDZSFJQIGHW-UHFFFAOYSA-N 0.000 description 1
• LPBKLQPAEHMOSD-UHFFFAOYSA-N methyl 9-benzyl-7-ethyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1 LPBKLQPAEHMOSD-UHFFFAOYSA-N 0.000 description 1
• NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 description 1
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• FSUMZUVANZAHBW-UHFFFAOYSA-N n,n-dimethoxyaniline Chemical compound CON(OC)C1=CC=CC=C1 FSUMZUVANZAHBW-UHFFFAOYSA-N 0.000 description 1
• NPKYYJGDHWBTSU-UHFFFAOYSA-N n-benzyl-3,5-dimethoxyaniline Chemical compound COC1=CC(OC)=CC(NCC=2C=CC=CC=2)=C1 NPKYYJGDHWBTSU-UHFFFAOYSA-N 0.000 description 1
• RPYFXGGUZSMKST-UHFFFAOYSA-N n-cyclotetradecyl-1-methyl-9h-carbazole-4-carboxamide Chemical compound N1C2=CC=CC=C2C2=C1C(C)=CC=C2C(=O)NC1CCCCCCCCCCCCC1 RPYFXGGUZSMKST-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
• 150000002829 nitrogen Chemical class 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• 239000012454 non-polar solvent Substances 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000005593 norbornanyl group Chemical group 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 125000000962 organic group Chemical group 0.000 description 1
• 238000012261 overproduction Methods 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
• 125000005981 pentynyl group Chemical group 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 239000003444 phase transfer catalyst Substances 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 125000003884 phenylalkyl group Chemical group 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004344 phenylpropyl group Chemical group 0.000 description 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 150000003003 phosphines Chemical class 0.000 description 1
• 150000003904 phospholipids Chemical class 0.000 description 1
• 125000005499 phosphonyl group Chemical group 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 125000003367 polycyclic group Chemical group 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• WSXVMAZXAYSHMK-UHFFFAOYSA-N propan-2-yl 1-[3-(dimethylamino)propyl]-8-ethoxy-5-(hydrazinecarbonyl)-9-methylcarbazole-3-carboxylate Chemical compound C12=CC(C(=O)OC(C)C)=CC(CCCN(C)C)=C2N(C)C2=C1C(C(=O)NN)=CC=C2OCC WSXVMAZXAYSHMK-UHFFFAOYSA-N 0.000 description 1
• NNBSNJRZVRNCGX-UHFFFAOYSA-N propyl 2-[[5-(hydrazinecarbonyl)-9-(3-methoxy-5-propan-2-ylphenyl)-8-methyl-5,6,7,8-tetrahydrocarbazol-3-yl]oxy]acetate Chemical compound C1=2C(C)CCC(C(=O)NN)C=2C2=CC(OCC(=O)OCCC)=CC=C2N1C1=CC(OC)=CC(C(C)C)=C1 NNBSNJRZVRNCGX-UHFFFAOYSA-N 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
• 239000000523 sample Substances 0.000 description 1
• 230000003248 secreting effect Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
• 229940075931 sodium dithionate Drugs 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• LKFFKHLNCCHRLE-UHFFFAOYSA-M sodium;2-(9-benzyl-5-carbamoyl-2-methylcarbazol-4-yl)oxyacetate Chemical compound [Na+].C=1C(C)=CC(OCC([O-])=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 LKFFKHLNCCHRLE-UHFFFAOYSA-M 0.000 description 1
• 238000003797 solvolysis reaction Methods 0.000 description 1
• 238000004544 sputter deposition Methods 0.000 description 1
• 230000000707 stereoselective effect Effects 0.000 description 1
• 230000035882 stress Effects 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 230000006103 sulfonylation Effects 0.000 description 1
• 238000005694 sulfonylation reaction Methods 0.000 description 1
• 125000004434 sulfur atom Chemical group 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
• ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
• HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
• DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
• 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 150000005671 trienes Chemical class 0.000 description 1
• BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
• IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
• RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
• GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
• IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000007738 vacuum evaporation Methods 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1
• 150000003738 xylenes Chemical class 0.000 description 1
• 239000011592 zinc chloride Substances 0.000 description 1
• 235000005074 zinc chloride Nutrition 0.000 description 1