CA2269262A1 - Substituted tricyclics - Google Patents

Info

Publication number

CA2269262A1

CA2269262A1 CA002269262A CA2269262A CA2269262A1 CA 2269262 A1 CA2269262 A1 CA 2269262A1 CA 002269262 A CA002269262 A CA 002269262A CA 2269262 A CA2269262 A CA 2269262A CA 2269262 A1 CA2269262 A1 CA 2269262A1

Authority

CA

Canada

Prior art keywords

methyl

alkyl

phenyl

oxyacetic acid

carbamoyl

Prior art date

1998-04-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 claims abstract description 152
• 102000005473 Secretory Phospholipases A2 Human genes 0.000 claims abstract 13
• 108010031873 Secretory Phospholipases A2 Proteins 0.000 claims abstract 13
• 206010040070 Septic Shock Diseases 0.000 claims abstract 8
• 230000036303 septic shock Effects 0.000 claims abstract 8
• 230000002401 inhibitory effect Effects 0.000 claims abstract 7
• 235000014113 dietary fatty acids Nutrition 0.000 claims abstract 3
• 229930195729 fatty acid Natural products 0.000 claims abstract 3
• 239000000194 fatty acid Substances 0.000 claims abstract 3
• 150000004665 fatty acids Chemical class 0.000 claims abstract 3
• 230000001404 mediated effect Effects 0.000 claims abstract 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 710
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 132
• 239000002253 acid Substances 0.000 claims description 105
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 98
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 73
• -1 carbocyclic radicals Chemical class 0.000 claims description 64
• 150000004702 methyl esters Chemical class 0.000 claims description 45
• 238000000034 method Methods 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 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 31
• 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 description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 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 claims description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• 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 8
• 125000004494 ethyl ester group Chemical group 0.000 claims description 7
• OJRRWHBSOZGENJ-UHFFFAOYSA-N 2-[5-carbamoyl-9-(pyridin-3-ylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CN=C1 OJRRWHBSOZGENJ-UHFFFAOYSA-N 0.000 claims description 6
• 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 claims description 6
• 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 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 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 claims description 5
• 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 claims description 5
• HCQNYAIKYZCDBC-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-propan-2-ylcarbazol-4-yl)oxyacetic acid Chemical compound C=1C(C(C)C)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 HCQNYAIKYZCDBC-UHFFFAOYSA-N 0.000 claims description 5
• UFJILQXRMNERCL-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoylcarbazol-4-yl)oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 UFJILQXRMNERCL-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 5
• BLCNILYGCATZEH-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2,3-difluorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(F)=C1F BLCNILYGCATZEH-UHFFFAOYSA-N 0.000 claims description 5
• VRMKRGKLFIJSNY-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2,6-difluorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=C(F)C=CC=C1F VRMKRGKLFIJSNY-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 5
• MQZAJAXITWPMFM-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-fluorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1F MQZAJAXITWPMFM-UHFFFAOYSA-N 0.000 claims description 5
• YAENEAAYRCUGQB-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3,5-dimethylphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound CC1=CC(C)=CC(CN2C3=CC=CC(=C3C3=C(OCC(O)=O)C=CC=C32)C(N)=O)=C1 YAENEAAYRCUGQB-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 5
• 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 claims description 5
• FRZSYHNHELRNDK-UHFFFAOYSA-N 2-[9-[(2-benzylphenyl)methyl]-5-carbamoylcarbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 FRZSYHNHELRNDK-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 5
• 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 5
• 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 5
• XRRDFIPYLFCYLU-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical group [CH2]C1=CC(C)=CC(C)=C1 XRRDFIPYLFCYLU-UHFFFAOYSA-N 0.000 claims description 4
• HWVCTTFKEFUZSR-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-phenylcarbazol-4-yl)oxyacetic acid Chemical compound C12=CC(C=3C=CC=CC=3)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 HWVCTTFKEFUZSR-UHFFFAOYSA-N 0.000 claims description 4
• 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 claims 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 claims description 4
• URFXAPISJQEWEH-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2,6-dichlorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl URFXAPISJQEWEH-UHFFFAOYSA-N 0.000 claims description 4
• UJSZZKJIGGAMHM-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-methylphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound CC1=CC=CC=C1CN1C2=CC=CC(C(N)=O)=C2C2=C(OCC(O)=O)C=CC=C21 UJSZZKJIGGAMHM-UHFFFAOYSA-N 0.000 claims description 4
• 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 claims description 4
• IKVWXTBYJHSVHF-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound CC1=CC=CC(CN2C3=CC=CC(=C3C3=C(OCC(O)=O)C=CC=C32)C(N)=O)=C1 IKVWXTBYJHSVHF-UHFFFAOYSA-N 0.000 claims description 4
• JCJMBFNXBWSTLL-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-phenoxyphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 JCJMBFNXBWSTLL-UHFFFAOYSA-N 0.000 claims description 4
• GCOWGWQVPARYNI-UHFFFAOYSA-N 2-[5-carbamoyl-9-[[3-(trifluoromethoxy)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(OC(F)(F)F)=C1 GCOWGWQVPARYNI-UHFFFAOYSA-N 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 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 claims description 4
• 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 claims description 4
• IPUAVVIZGWPBKH-UHFFFAOYSA-N 9-benzyl-5-hydroxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound NC(=O)C1CCCC2=C1C1=C(O)C=CC=C1N2CC1=CC=CC=C1 IPUAVVIZGWPBKH-UHFFFAOYSA-N 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 229910003002 lithium salt Inorganic materials 0.000 claims description 4
• 159000000002 lithium salts Chemical class 0.000 claims description 4
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
• PHRABVHYUHIYGY-UHFFFAOYSA-N 1-methylnaphthalene Chemical group C1=CC=C2C([CH2])=CC=CC2=C1 PHRABVHYUHIYGY-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• XQHXEBCEJGFYFD-UHFFFAOYSA-N 2-[5-carbamoyl-9-(cyclohexylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1CCCCC1 XQHXEBCEJGFYFD-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• KWBVGNHCBQIRTN-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-fluorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(F)=C1 KWBVGNHCBQIRTN-UHFFFAOYSA-N 0.000 claims description 3
• NDTBXYQGBBMXLW-UHFFFAOYSA-N 2-[5-carbamoyl-9-[[3-(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(C(F)(F)F)=C1 NDTBXYQGBBMXLW-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 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 3
• 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 3
• 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 description 3
• 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 description 3
• QIBDSPVXVMCOLO-UHFFFAOYSA-N 9-benzyl-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid Chemical compound C1=2CCCC(C(O)=O)C=2C=2C(OC)=CC=CC=2N1CC1=CC=CC=C1 QIBDSPVXVMCOLO-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• PRAUIYBTAAOMCZ-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-methoxycarbazol-4-yl)oxypropanoic acid Chemical compound C=1C(OC)=CC(OC(C)C(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 PRAUIYBTAAOMCZ-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• PYNUQYVAXQHNAJ-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-2-methoxy-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound C12=CC(OC)=CC(OCC(O)=O)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 PYNUQYVAXQHNAJ-UHFFFAOYSA-N 0.000 claims description 2
• YFTJSPAAYBFQNI-UHFFFAOYSA-N 2-[5-carbamoyl-9-(cyclopentylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1CCCC1 YFTJSPAAYBFQNI-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims description 2
• RLYWCMMWDHISRY-UHFFFAOYSA-N 9-benzyl-5-hydroxy-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid Chemical compound OC(=O)C1CCCC2=C1C1=C(O)C=CC=C1N2CC1=CC=CC=C1 RLYWCMMWDHISRY-UHFFFAOYSA-N 0.000 claims description 2
• WMHDZBMBPZASPI-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-[tri(propan-2-yl)silyloxymethyl]carbazole-4-carboxamide Chemical compound C=1C(CO[Si](C(C)C)(C(C)C)C(C)C)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 WMHDZBMBPZASPI-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
• 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
• 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 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
• 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
• 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 description 2
• IHPUOZMXJDHIBO-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-1-fluorocarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=C(F)C=2N1CC1=CC=CC=C1 IHPUOZMXJDHIBO-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
• 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
• ZPNGYRPSWVQROU-UHFFFAOYSA-N methyl 7-(furan-2-yl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=CO1 ZPNGYRPSWVQROU-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 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
• 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 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
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• DRRPBTBDXRFNRV-UHFFFAOYSA-N 5-hydroxy-7-methyl-8-[(3-methylphenyl)methyl]-9h-carbazole-4-carboxamide Chemical compound CC1=CC=CC(CC=2C3=C(C4=C(C(N)=O)C=CC=C4N3)C(O)=CC=2C)=C1 DRRPBTBDXRFNRV-UHFFFAOYSA-N 0.000 claims 1
• PKWKOZFVBKURBY-UHFFFAOYSA-N 5-hydroxy-8-(pyridin-2-ylmethyl)-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=N1 PKWKOZFVBKURBY-UHFFFAOYSA-N 0.000 claims 1
• KHDBUZYUKAXECE-UHFFFAOYSA-N 5-hydroxy-8-(pyridin-3-ylmethyl)-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CN=C1 KHDBUZYUKAXECE-UHFFFAOYSA-N 0.000 claims 1
• MFIXRNRZGPNXSH-UHFFFAOYSA-N 5-hydroxy-8-[(2-methylphenyl)methyl]-9h-carbazole-4-carboxamide Chemical compound CC1=CC=CC=C1CC1=CC=C(O)C2=C1NC1=CC=CC(C(N)=O)=C21 MFIXRNRZGPNXSH-UHFFFAOYSA-N 0.000 claims 1
• HZXRZFGEOLILIJ-UHFFFAOYSA-N 5-hydroxy-8-[(3-iodophenyl)methyl]-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(I)=C1 HZXRZFGEOLILIJ-UHFFFAOYSA-N 0.000 claims 1
• INNFVKUFMBJSQG-UHFFFAOYSA-N 5-hydroxy-8-[(3-methylphenyl)methyl]-9h-carbazole-4-carboxamide Chemical compound CC1=CC=CC(CC=2C3=C(C4=C(C(N)=O)C=CC=C4N3)C(O)=CC=2)=C1 INNFVKUFMBJSQG-UHFFFAOYSA-N 0.000 claims 1
• SKHRIGNKPWCVGR-UHFFFAOYSA-N 5-hydroxy-8-[(3-phenoxyphenyl)methyl]-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC(C=1)=CC=CC=1OC1=CC=CC=C1 SKHRIGNKPWCVGR-UHFFFAOYSA-N 0.000 claims 1
• BWYVEKNFBOTPPC-UHFFFAOYSA-N 5-hydroxy-8-[[2-(trifluoromethyl)phenyl]methyl]-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=C1C(F)(F)F BWYVEKNFBOTPPC-UHFFFAOYSA-N 0.000 claims 1
• RHLYVBWOJXIJDL-UHFFFAOYSA-N 5-hydroxy-8-[[3-(trifluoromethoxy)phenyl]methyl]-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(OC(F)(F)F)=C1 RHLYVBWOJXIJDL-UHFFFAOYSA-N 0.000 claims 1
• HIXZOUQNFRLFFJ-UHFFFAOYSA-N 5-hydroxy-8-[[3-(trifluoromethyl)phenyl]methyl]-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(C(F)(F)F)=C1 HIXZOUQNFRLFFJ-UHFFFAOYSA-N 0.000 claims 1
• MMYKUAMFENGBBP-UHFFFAOYSA-N 8-(cyclohexylmethyl)-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1CCCCC1 MMYKUAMFENGBBP-UHFFFAOYSA-N 0.000 claims 1
• QOLJQZMMHKRZMO-UHFFFAOYSA-N 8-[(2,3-difluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(F)=C1F QOLJQZMMHKRZMO-UHFFFAOYSA-N 0.000 claims 1
• FGKZMJGWYWKLBQ-UHFFFAOYSA-N 8-[(2,6-dichlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=C(Cl)C=CC=C1Cl FGKZMJGWYWKLBQ-UHFFFAOYSA-N 0.000 claims 1
• UCGVINSTSFZFAV-UHFFFAOYSA-N 8-[(2-benzylphenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=C1CC1=CC=CC=C1 UCGVINSTSFZFAV-UHFFFAOYSA-N 0.000 claims 1
• ZTRFJOQLJWSGSD-UHFFFAOYSA-N 8-[(2-chlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=C1Cl ZTRFJOQLJWSGSD-UHFFFAOYSA-N 0.000 claims 1
• LARGYAUQGJESEN-UHFFFAOYSA-N 8-[(2-cyanophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=C1C#N LARGYAUQGJESEN-UHFFFAOYSA-N 0.000 claims 1
• WQEJWGBMYOKNOY-UHFFFAOYSA-N 8-[(2-fluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=C1F WQEJWGBMYOKNOY-UHFFFAOYSA-N 0.000 claims 1
• BBLCQUWUBSVOQS-UHFFFAOYSA-N 8-[(3-chlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(Cl)=C1 BBLCQUWUBSVOQS-UHFFFAOYSA-N 0.000 claims 1
• BHAJYOWNSKSYJB-UHFFFAOYSA-N 8-[(3-cyanophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(C#N)=C1 BHAJYOWNSKSYJB-UHFFFAOYSA-N 0.000 claims 1
• ZGFFRTMYHWPHRN-UHFFFAOYSA-N 8-[(3-fluorophenyl)methyl]-5-hydroxy-7-methyl-9h-carbazole-4-carboxamide Chemical compound CC1=CC(O)=C(C2=C(C(N)=O)C=CC=C2N2)C2=C1CC1=CC=CC(F)=C1 ZGFFRTMYHWPHRN-UHFFFAOYSA-N 0.000 claims 1
• DCDSYOQEGRYCNZ-UHFFFAOYSA-N 8-[(3-fluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(F)=C1 DCDSYOQEGRYCNZ-UHFFFAOYSA-N 0.000 claims 1
• HNNUYSGYYDKVIQ-UHFFFAOYSA-N 8-benzyl-5-hydroxy-7-[4-(trifluoromethyl)phenyl]-9h-carbazole-4-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=C1 HNNUYSGYYDKVIQ-UHFFFAOYSA-N 0.000 claims 1
• PBPXPVULSRZWRM-UHFFFAOYSA-N 8-benzyl-5-hydroxy-7-methyl-9h-carbazole-4-carboxamide Chemical compound CC1=CC(O)=C(C2=C(C(N)=O)C=CC=C2N2)C2=C1CC1=CC=CC=C1 PBPXPVULSRZWRM-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• WHMJBMNTVKVVOQ-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C12=CC(OC)=CC(O)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 WHMJBMNTVKVVOQ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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
• 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
• 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 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
• BHHQJKFYUSXYTH-UHFFFAOYSA-N C1(=CC=CC=C1)CC1=CC=C(C=2C3=C(C=CC=C3NC12)C(N)=O)O.C1(=CC=CC=C1)CC1=CC=C(C=2C3=C(C=CC=C3NC12)C(=O)OC)O Chemical compound C1(=CC=CC=C1)CC1=CC=C(C=2C3=C(C=CC=C3NC12)C(N)=O)O.C1(=CC=CC=C1)CC1=CC=C(C=2C3=C(C=CC=C3NC12)C(=O)OC)O BHHQJKFYUSXYTH-UHFFFAOYSA-N 0.000 claims 1
• DYXWBNIMHQRLCQ-UHFFFAOYSA-N COC(COC1=CC=C(C=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=CC=CC=C1)Cl)=O.COC(COC1=CC=C(C=2NC3=CC=CC(=C3C12)C(N)=O)Cl)=O Chemical compound COC(COC1=CC=C(C=2N(C3=CC=CC(=C3C12)C(N)=O)CC1=CC=CC=C1)Cl)=O.COC(COC1=CC=C(C=2NC3=CC=CC(=C3C12)C(N)=O)Cl)=O DYXWBNIMHQRLCQ-UHFFFAOYSA-N 0.000 claims 1
• 125000003545 alkoxy group Chemical group 0.000 claims 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
• 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 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• 230000003301 hydrolyzing effect Effects 0.000 claims 1
• ANUWEGZYNYTFIU-UHFFFAOYSA-N methyl 2-[(9-benzyl-5-carbamoyl-1-fluoro-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetate Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OCC(=O)OC)=CC=C(F)C=2N1CC1=CC=CC=C1 ANUWEGZYNYTFIU-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
• LGXOONHKKWGSAJ-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-8-[(3-methylphenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound CC1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(C)=C1 LGXOONHKKWGSAJ-UHFFFAOYSA-N 0.000 claims 1
• XDKCFHNIBOULLE-UHFFFAOYSA-N methyl 5-hydroxy-8-(naphthalen-1-ylmethyl)-9h-carbazole-4-carboxylate Chemical compound C1=CC=C2C(CC3=C4NC=5C=CC=C(C=5C4=C(O)C=C3)C(=O)OC)=CC=CC2=C1 XDKCFHNIBOULLE-UHFFFAOYSA-N 0.000 claims 1
• DRBWJKXGTZSNRR-UHFFFAOYSA-N methyl 5-hydroxy-8-(pyridin-2-ylmethyl)-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=N1 DRBWJKXGTZSNRR-UHFFFAOYSA-N 0.000 claims 1
• MJMQBPVZKYFGNI-UHFFFAOYSA-N methyl 5-hydroxy-8-(pyridin-3-ylmethyl)-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CN=C1 MJMQBPVZKYFGNI-UHFFFAOYSA-N 0.000 claims 1
• KYNVMTIOCYUILP-UHFFFAOYSA-N methyl 5-hydroxy-8-[(2-methylphenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1C KYNVMTIOCYUILP-UHFFFAOYSA-N 0.000 claims 1
• OCPKAVXMHCEGPV-UHFFFAOYSA-N methyl 5-hydroxy-8-[(3-iodophenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(I)=C1 OCPKAVXMHCEGPV-UHFFFAOYSA-N 0.000 claims 1
• JYKZPQXYQAZBDW-UHFFFAOYSA-N methyl 5-hydroxy-8-[(3-methylphenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(C)=C1 JYKZPQXYQAZBDW-UHFFFAOYSA-N 0.000 claims 1
• FPTBZQSEQNTANC-UHFFFAOYSA-N methyl 5-hydroxy-8-[(3-phenoxyphenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC(C=1)=CC=CC=1OC1=CC=CC=C1 FPTBZQSEQNTANC-UHFFFAOYSA-N 0.000 claims 1
• NFKZUNBTGGOYET-UHFFFAOYSA-N methyl 5-hydroxy-8-[[2-(trifluoromethyl)phenyl]methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1C(F)(F)F NFKZUNBTGGOYET-UHFFFAOYSA-N 0.000 claims 1
• YAAFHPCNTNTEEB-UHFFFAOYSA-N methyl 5-hydroxy-8-[[3-(trifluoromethoxy)phenyl]methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(OC(F)(F)F)=C1 YAAFHPCNTNTEEB-UHFFFAOYSA-N 0.000 claims 1
• GEHIQDZATHASGF-UHFFFAOYSA-N methyl 5-hydroxy-8-[[3-(trifluoromethyl)phenyl]methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(C(F)(F)F)=C1 GEHIQDZATHASGF-UHFFFAOYSA-N 0.000 claims 1
• QMZHGZNTWCWPKL-UHFFFAOYSA-N methyl 5-oxo-8-(pyridin-2-ylmethyl)-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=N1 QMZHGZNTWCWPKL-UHFFFAOYSA-N 0.000 claims 1
• VYTNZQJWZUYBQE-UHFFFAOYSA-N methyl 5-oxo-8-(pyridin-3-ylmethyl)-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CN=C1 VYTNZQJWZUYBQE-UHFFFAOYSA-N 0.000 claims 1
• MUJYXSFRZGCNOZ-UHFFFAOYSA-N methyl 5-oxo-8-[(3-phenoxyphenyl)methyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC(C=1)=CC=CC=1OC1=CC=CC=C1 MUJYXSFRZGCNOZ-UHFFFAOYSA-N 0.000 claims 1
• IPJFPRBENXFRAM-UHFFFAOYSA-N methyl 5-oxo-8-[[2-(trifluoromethyl)phenyl]methyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1C(F)(F)F IPJFPRBENXFRAM-UHFFFAOYSA-N 0.000 claims 1
• FJZREPYGVSKYKK-UHFFFAOYSA-N methyl 5-oxo-8-[[3-(trifluoromethoxy)phenyl]methyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(OC(F)(F)F)=C1 FJZREPYGVSKYKK-UHFFFAOYSA-N 0.000 claims 1
• LVQOUDKUNKIAAY-UHFFFAOYSA-N methyl 5-oxo-8-[[3-(trifluoromethyl)phenyl]methyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(C(F)(F)F)=C1 LVQOUDKUNKIAAY-UHFFFAOYSA-N 0.000 claims 1
• BHPDQZPWRCGIIW-UHFFFAOYSA-N methyl 7-methyl-8-[(3-methylphenyl)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(C)=C1 BHPDQZPWRCGIIW-UHFFFAOYSA-N 0.000 claims 1
• GEZZVZOTGGOQOF-UHFFFAOYSA-N methyl 8-(cyclohexylmethyl)-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1CCCCC1 GEZZVZOTGGOQOF-UHFFFAOYSA-N 0.000 claims 1
• HCKOATMSEPUWTK-UHFFFAOYSA-N methyl 8-(cyclohexylmethyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1CCCCC1 HCKOATMSEPUWTK-UHFFFAOYSA-N 0.000 claims 1
• SUYVZIOYJWVSJW-UHFFFAOYSA-N methyl 8-(cyclopentylmethyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1CCCC1 SUYVZIOYJWVSJW-UHFFFAOYSA-N 0.000 claims 1
• KFDVBCLAXUUVGA-UHFFFAOYSA-N methyl 8-(naphthalen-1-ylmethyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1=CC=C2C(CC3C=4NC=5C=CC=C(C=5C=4C(=O)CC3)C(=O)OC)=CC=CC2=C1 KFDVBCLAXUUVGA-UHFFFAOYSA-N 0.000 claims 1
• QYLCAWWPPICHHY-UHFFFAOYSA-N methyl 8-[(2,3-difluorophenyl)methyl]-5-hydroxy-9H-carbazole-4-carboxylate Chemical compound FC1=C(C=CC=C1F)CC1=CC=C(C=2C3=C(C=CC=C3NC12)C(=O)OC)O QYLCAWWPPICHHY-UHFFFAOYSA-N 0.000 claims 1
• ZEJPSGCVVKNPPK-UHFFFAOYSA-N methyl 8-[(2,3-difluorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(F)=C1F ZEJPSGCVVKNPPK-UHFFFAOYSA-N 0.000 claims 1
• OIVCMCCYGDDZIW-UHFFFAOYSA-N methyl 8-[(2,6-dichlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=C(Cl)C=CC=C1Cl OIVCMCCYGDDZIW-UHFFFAOYSA-N 0.000 claims 1
• GXTUYYOXXRWXHH-UHFFFAOYSA-N methyl 8-[(2,6-dichlorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=C(Cl)C=CC=C1Cl GXTUYYOXXRWXHH-UHFFFAOYSA-N 0.000 claims 1
• LSPMHPSRUGWPOU-UHFFFAOYSA-N methyl 8-[(2,6-difluorophenyl)methyl]-5-hydroxy-9H-carbazole-4-carboxylate methyl 8-[(2,6-difluorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound FC1=C(C(=CC=C1)F)CC1=CC=C(C=2C3=C(C=CC=C3NC12)C(=O)OC)O.FC1=C(C(=CC=C1)F)CC1CCC(C=2C3=C(C=CC=C3NC12)C(=O)OC)=O LSPMHPSRUGWPOU-UHFFFAOYSA-N 0.000 claims 1
• ZRCUHIXGCNCATB-UHFFFAOYSA-N methyl 8-[(2-benzylphenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1CC1=CC=CC=C1 ZRCUHIXGCNCATB-UHFFFAOYSA-N 0.000 claims 1
• VTRPEPBNRKALSA-UHFFFAOYSA-N methyl 8-[(2-benzylphenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1CC1=CC=CC=C1 VTRPEPBNRKALSA-UHFFFAOYSA-N 0.000 claims 1
• CMTJUHAPNXOKMH-UHFFFAOYSA-N methyl 8-[(2-chlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1Cl CMTJUHAPNXOKMH-UHFFFAOYSA-N 0.000 claims 1
• XCGUNJVHYPYOLO-UHFFFAOYSA-N methyl 8-[(2-chlorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1Cl XCGUNJVHYPYOLO-UHFFFAOYSA-N 0.000 claims 1
• QMOMLSDZBQSOKC-UHFFFAOYSA-N methyl 8-[(2-cyanophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1C#N QMOMLSDZBQSOKC-UHFFFAOYSA-N 0.000 claims 1
• PJNHGSLSWGGCJL-UHFFFAOYSA-N methyl 8-[(2-cyanophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1C#N PJNHGSLSWGGCJL-UHFFFAOYSA-N 0.000 claims 1
• IPMOWRZNUJLVIJ-UHFFFAOYSA-N methyl 8-[(2-fluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1F IPMOWRZNUJLVIJ-UHFFFAOYSA-N 0.000 claims 1
• PSUWMGDNEDHTRX-UHFFFAOYSA-N methyl 8-[(2-fluorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1F PSUWMGDNEDHTRX-UHFFFAOYSA-N 0.000 claims 1
• MZRRZOWIEKWCDJ-UHFFFAOYSA-N methyl 8-[(3,5-dimethylphenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC(C)=CC(C)=C1 MZRRZOWIEKWCDJ-UHFFFAOYSA-N 0.000 claims 1
• RWQODNUXKYOHEQ-UHFFFAOYSA-N methyl 8-[(3,5-dimethylphenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC(C)=CC(C)=C1 RWQODNUXKYOHEQ-UHFFFAOYSA-N 0.000 claims 1
• NCFKVOYLJUVJPQ-UHFFFAOYSA-N methyl 8-[(3-chlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(Cl)=C1 NCFKVOYLJUVJPQ-UHFFFAOYSA-N 0.000 claims 1
• QIBDGTAYYPRPBS-UHFFFAOYSA-N methyl 8-[(3-chlorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(Cl)=C1 QIBDGTAYYPRPBS-UHFFFAOYSA-N 0.000 claims 1
• UTVOHZWCZSBNHV-UHFFFAOYSA-N methyl 8-[(3-cyanophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(C#N)=C1 UTVOHZWCZSBNHV-UHFFFAOYSA-N 0.000 claims 1
• PAMLAIMRXGQXDB-UHFFFAOYSA-N methyl 8-[(3-cyanophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(C#N)=C1 PAMLAIMRXGQXDB-UHFFFAOYSA-N 0.000 claims 1
• LLJBLIUDIZNGAE-UHFFFAOYSA-N methyl 8-[(3-fluorophenyl)methyl]-5-hydroxy-7-methyl-9h-carbazole-4-carboxylate Chemical compound CC1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(F)=C1 LLJBLIUDIZNGAE-UHFFFAOYSA-N 0.000 claims 1
• OIDBVEJMWHVFOC-UHFFFAOYSA-N methyl 8-[(3-fluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(F)=C1 OIDBVEJMWHVFOC-UHFFFAOYSA-N 0.000 claims 1
• NSQRKYXXYKOQDY-UHFFFAOYSA-N methyl 8-[(3-fluorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(F)=C1 NSQRKYXXYKOQDY-UHFFFAOYSA-N 0.000 claims 1
• JDFGJZQZTOSUOE-UHFFFAOYSA-N methyl 8-[(3-fluorophenyl)methyl]-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(F)=C1 JDFGJZQZTOSUOE-UHFFFAOYSA-N 0.000 claims 1
• MYSACBDANIYOTO-UHFFFAOYSA-N methyl 8-[(3-iodophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(I)=C1 MYSACBDANIYOTO-UHFFFAOYSA-N 0.000 claims 1
• JADWBCSDSKRQQP-UHFFFAOYSA-N methyl 8-[(3-methylphenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(C)=C1 JADWBCSDSKRQQP-UHFFFAOYSA-N 0.000 claims 1
• UOJWZSYHSNVSCI-UHFFFAOYSA-N methyl 8-benzyl-5-hydroxy-7-[4-(trifluoromethyl)phenyl]-9h-carbazole-4-carboxylate Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1 UOJWZSYHSNVSCI-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
• UUTJGUDEDSFFHG-UHFFFAOYSA-N methyl 8-benzyl-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1 UUTJGUDEDSFFHG-UHFFFAOYSA-N 0.000 claims 1
• BHDFQVHWKNUUBP-UHFFFAOYSA-N methyl 8-benzyl-5-oxo-7-[4-(trifluoromethyl)phenyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1 BHDFQVHWKNUUBP-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
• 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 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
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 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 claims 1
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 259
• 235000019439 ethyl acetate Nutrition 0.000 description 251
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 228
• 238000000921 elemental analysis Methods 0.000 description 199
• 239000000203 mixture Substances 0.000 description 199
• 239000000243 solution Substances 0.000 description 186
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 184
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 169
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 159
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 156
• 238000005160 1H NMR spectroscopy Methods 0.000 description 136
• 238000002360 preparation method Methods 0.000 description 136
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 135
• 239000007787 solid Substances 0.000 description 133
• 239000000741 silica gel Substances 0.000 description 128
• 229910002027 silica gel Inorganic materials 0.000 description 128
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 117
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 115
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 104
• 101150041968 CDC13 gene Proteins 0.000 description 100
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 100
• 238000010828 elution Methods 0.000 description 98
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 93
• 238000005481 NMR spectroscopy Methods 0.000 description 84
• 238000004440 column chromatography Methods 0.000 description 82
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 68
• 235000019341 magnesium sulphate Nutrition 0.000 description 68
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 63
• 238000006243 chemical reaction Methods 0.000 description 56
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• 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 52
• 239000000725 suspension Substances 0.000 description 50
• 239000010410 layer Substances 0.000 description 49
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 46
• 239000011369 resultant mixture Substances 0.000 description 44
• 239000000284 extract Substances 0.000 description 41
• 239000012267 brine Substances 0.000 description 40
• 159000000000 sodium salts Chemical class 0.000 description 39
• 238000001914 filtration Methods 0.000 description 35
• 239000002244 precipitate Substances 0.000 description 34
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 31
• 235000011114 ammonium hydroxide Nutrition 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 239000000908 ammonium hydroxide Substances 0.000 description 30
• NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 30
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 30
• YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 29
• 239000012044 organic layer Substances 0.000 description 29
• 239000000843 powder Substances 0.000 description 28
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• 239000000047 product Substances 0.000 description 24
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 24
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 23
• 239000003921 oil Substances 0.000 description 23
• 229910000027 potassium carbonate Inorganic materials 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 22
• 238000003756 stirring Methods 0.000 description 21
• 239000006260 foam Substances 0.000 description 19
• 229910000104 sodium hydride Inorganic materials 0.000 description 19
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 18
• 239000012312 sodium hydride Substances 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
• 239000002480 mineral oil Substances 0.000 description 16
• 235000010446 mineral oil Nutrition 0.000 description 16
• 229910052938 sodium sulfate Inorganic materials 0.000 description 16
• 235000011152 sodium sulphate Nutrition 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• 239000011541 reaction mixture Substances 0.000 description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• NIXWZYZFLFEHMB-UHFFFAOYSA-N methyl 3-amino-2-bromobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1Br NIXWZYZFLFEHMB-UHFFFAOYSA-N 0.000 description 12
• 238000010992 reflux Methods 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 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 10
• 239000000377 silicon dioxide Substances 0.000 description 10
• 239000007858 starting material Substances 0.000 description 10
• 229910000024 caesium carbonate Inorganic materials 0.000 description 9
• 238000001704 evaporation Methods 0.000 description 9
• 230000008020 evaporation Effects 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 8
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
• 238000002474 experimental method Methods 0.000 description 8
• 239000012299 nitrogen atmosphere Substances 0.000 description 8
• 235000009518 sodium iodide Nutrition 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 7
• 238000001035 drying Methods 0.000 description 7
• NKBQKMXNIWIFAE-UHFFFAOYSA-N methyl 3-amino-2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1Cl NKBQKMXNIWIFAE-UHFFFAOYSA-N 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• WTDJEGSXLFHZPY-UHFFFAOYSA-N 2-bromo-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1Br WTDJEGSXLFHZPY-UHFFFAOYSA-N 0.000 description 6
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 6
• 229960000583 acetic acid Drugs 0.000 description 6
• 239000007789 gas Substances 0.000 description 6
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
• JBCQPBVZKBEHNF-UHFFFAOYSA-N methyl 2-chloro-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1Cl JBCQPBVZKBEHNF-UHFFFAOYSA-N 0.000 description 6
• PSNSVDSRLUYDKF-UHFFFAOYSA-N methyl benzenesulfinate Chemical compound COS(=O)C1=CC=CC=C1 PSNSVDSRLUYDKF-UHFFFAOYSA-N 0.000 description 6
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 239000002002 slurry Substances 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 6
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 230000003197 catalytic effect Effects 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 238000004128 high performance liquid chromatography Methods 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 5
• 238000001665 trituration Methods 0.000 description 5
• 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 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• 238000004458 analytical method Methods 0.000 description 4
• NQIIILQXTJXSCA-UHFFFAOYSA-N chloromethylcyclopentane Chemical compound ClCC1CCCC1 NQIIILQXTJXSCA-UHFFFAOYSA-N 0.000 description 4
• 238000011097 chromatography purification Methods 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 238000003818 flash chromatography Methods 0.000 description 4
• QFOIAPZFZSIQQU-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-(pyridin-2-ylmethyl)carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=N1 QFOIAPZFZSIQQU-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 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 description 4
• 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 description 4
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
• LMXVDOHKMVBODQ-UHFFFAOYSA-N 1-benzyl-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CC1=CC=CC=C1 LMXVDOHKMVBODQ-UHFFFAOYSA-N 0.000 description 3
• UIMGRPXPFBJHJJ-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-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(Cl)=C1 UIMGRPXPFBJHJJ-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• MBOMIENIHQGOAM-UHFFFAOYSA-N 5-hydroxy-9-(naphthalen-1-ylmethyl)carbazole-4-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC=CC(O)=C2C2=C1C=CC=C2C(=O)N MBOMIENIHQGOAM-UHFFFAOYSA-N 0.000 description 3
• UTSPAMRUMDHOIX-UHFFFAOYSA-N 5-hydroxy-9-(pyridin-2-ylmethyl)carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=N1 UTSPAMRUMDHOIX-UHFFFAOYSA-N 0.000 description 3
• RUEFNDMBRXTRPS-UHFFFAOYSA-N 5-hydroxy-9-(pyridin-3-ylmethyl)carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CN=C1 RUEFNDMBRXTRPS-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• ZQBMPCCWRBCRQX-UHFFFAOYSA-N 9-[(2,3-difluorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(F)=C1F ZQBMPCCWRBCRQX-UHFFFAOYSA-N 0.000 description 3
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• JRWSMGTUZSZVEN-UHFFFAOYSA-N 9-[(2-benzylphenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 JRWSMGTUZSZVEN-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• 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 description 3
• XCPQDLGZHDLIOI-UHFFFAOYSA-N 9-[(3,5-dimethylphenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound CC1=CC(C)=CC(CN2C3=CC=CC(=C3C3=C(O)C=CC=C32)C(N)=O)=C1 XCPQDLGZHDLIOI-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• XKGYMJJZCLTMRK-UHFFFAOYSA-N 9-benzyl-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=C1 XKGYMJJZCLTMRK-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• 101000909811 Homo sapiens Protein cornichon homolog 2 Proteins 0.000 description 3
• 102100024446 Protein cornichon homolog 2 Human genes 0.000 description 3
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
• 150000002085 enols Chemical class 0.000 description 3
• 238000000605 extraction Methods 0.000 description 3
• 238000000434 field desorption mass spectrometry Methods 0.000 description 3
• 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 3
• VYJSSWLKFMVSKB-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoylcarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 VYJSSWLKFMVSKB-UHFFFAOYSA-N 0.000 description 3
• ZKTFHYKIQRPLJK-UHFFFAOYSA-N methyl 2-[(9-benzyl-5-carbamoyl-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetate Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 ZKTFHYKIQRPLJK-UHFFFAOYSA-N 0.000 description 3
• FNUZWKBIAREHLD-UHFFFAOYSA-N methyl 2-[5-carbamoyl-2-methyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C)=CC=2N1CC1=CC=CC(C)=C1 FNUZWKBIAREHLD-UHFFFAOYSA-N 0.000 description 3
• NFMFPZIANORNMT-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-(naphthalen-1-ylmethyl)carbazol-4-yl]oxyacetate Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC=CC(C(N)=O)=C2C2=C1C=CC=C2OCC(=O)OC NFMFPZIANORNMT-UHFFFAOYSA-N 0.000 description 3
• LCJOXWCQHMXHCK-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2,3-difluorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1F LCJOXWCQHMXHCK-UHFFFAOYSA-N 0.000 description 3
• JKVDHSLQLFKKET-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2,6-dichlorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl JKVDHSLQLFKKET-UHFFFAOYSA-N 0.000 description 3
• OSDNLLDSSFQISV-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2,6-difluorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=C(F)C=CC=C1F OSDNLLDSSFQISV-UHFFFAOYSA-N 0.000 description 3
• HKHJMXGFWWRYGH-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2-cyanophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N HKHJMXGFWWRYGH-UHFFFAOYSA-N 0.000 description 3
• ADHVHSIJKWWKPA-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2-fluorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F ADHVHSIJKWWKPA-UHFFFAOYSA-N 0.000 description 3
• XHDSTXFXSCWLSF-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2-methylphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C XHDSTXFXSCWLSF-UHFFFAOYSA-N 0.000 description 3
• RKFXVRCQRMCWKM-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(3-fluorophenyl)methyl]-2-methylcarbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C)=CC=2N1CC1=CC=CC(F)=C1 RKFXVRCQRMCWKM-UHFFFAOYSA-N 0.000 description 3
• CHNIRPZCTJAGDW-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(3-iodophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(I)=C1 CHNIRPZCTJAGDW-UHFFFAOYSA-N 0.000 description 3
• DQVRYWNGCRCKPY-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 DQVRYWNGCRCKPY-UHFFFAOYSA-N 0.000 description 3
• PWRRXYOCPPBGMV-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[[2-(trifluoromethyl)phenyl]methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F PWRRXYOCPPBGMV-UHFFFAOYSA-N 0.000 description 3
• GBNZDHSCUSOAFU-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[[3-(trifluoromethoxy)phenyl]methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(OC(F)(F)F)=C1 GBNZDHSCUSOAFU-UHFFFAOYSA-N 0.000 description 3
• PENJYQTYSNGYMY-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[[3-(trifluoromethyl)phenyl]methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 PENJYQTYSNGYMY-UHFFFAOYSA-N 0.000 description 3
• SUUPRIMFSCSGTM-UHFFFAOYSA-N methyl 2-[9-[(2-benzylphenyl)methyl]-5-carbamoylcarbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 SUUPRIMFSCSGTM-UHFFFAOYSA-N 0.000 description 3
• RYAXFUQTWZDWQK-UHFFFAOYSA-N methyl 2-[9-benzyl-5-carbamoyl-2-[4-(trifluoromethyl)phenyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=2N1CC1=CC=CC=C1 RYAXFUQTWZDWQK-UHFFFAOYSA-N 0.000 description 3
• 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 3
• HBLWDERQOAUKGN-UHFFFAOYSA-N methyl 2-bromo-3-[(5-methyl-3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(C)CC(=O)C=2)=C1Br HBLWDERQOAUKGN-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• YBGBXOFBYJAQNA-UHFFFAOYSA-N methyl 5-oxo-9-(pyridin-2-ylmethyl)-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=N1 YBGBXOFBYJAQNA-UHFFFAOYSA-N 0.000 description 3
• MYCRKMVCEFJGCB-UHFFFAOYSA-N methyl 5-oxo-9-(pyridin-3-ylmethyl)-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CN=C1 MYCRKMVCEFJGCB-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• GSSRRPUGXNPLSG-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 GSSRRPUGXNPLSG-UHFFFAOYSA-N 0.000 description 3
• JVHMDDPXQAAJIT-UHFFFAOYSA-N methyl 9-benzyl-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=C1 JVHMDDPXQAAJIT-UHFFFAOYSA-N 0.000 description 3
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• DGBCEDABANLFFU-UHFFFAOYSA-N tert-butyl 2-[5-carbamoyl-9-[(2-chlorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC(C)(C)C)=CC=CC=2N1CC1=CC=CC=C1Cl DGBCEDABANLFFU-UHFFFAOYSA-N 0.000 description 3
• AMQKSDOYCMKXIW-UHFFFAOYSA-N tert-butyl 2-[5-carbamoyl-9-[(3-chlorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC(C)(C)C)=CC=CC=2N1CC1=CC=CC(Cl)=C1 AMQKSDOYCMKXIW-UHFFFAOYSA-N 0.000 description 3
• AJTKKJOHKMOBFD-UHFFFAOYSA-N tert-butyl 2-[5-carbamoyl-9-[(3-cyanophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC(C)(C)C)=CC=CC=2N1CC1=CC=CC(C#N)=C1 AJTKKJOHKMOBFD-UHFFFAOYSA-N 0.000 description 3
• PQLOIVOTHAHYNC-UHFFFAOYSA-N tert-butyl 2-[5-carbamoyl-9-[(3-phenoxyphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC(C)(C)C)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 PQLOIVOTHAHYNC-UHFFFAOYSA-N 0.000 description 3
• 239000011592 zinc chloride Substances 0.000 description 3
• 235000005074 zinc chloride Nutrition 0.000 description 3
• TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
• BGMMWAHLBZGOBB-UHFFFAOYSA-N (2-chloro-4-fluoro-5-nitrophenyl) ethyl carbonate Chemical compound CCOC(=O)OC1=CC([N+]([O-])=O)=C(F)C=C1Cl BGMMWAHLBZGOBB-UHFFFAOYSA-N 0.000 description 2
• YQKSSJXIMXARGI-UHFFFAOYSA-N (2-chloro-4-fluorophenyl) ethyl carbonate Chemical compound CCOC(=O)OC1=CC=C(F)C=C1Cl YQKSSJXIMXARGI-UHFFFAOYSA-N 0.000 description 2
• FWLWTILKTABGKQ-UHFFFAOYSA-N 1-(bromomethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CBr)=C1 FWLWTILKTABGKQ-UHFFFAOYSA-N 0.000 description 2
• CRONHBXGPYQWHX-UHFFFAOYSA-N 1-chloro-5-fluoro-2-methoxy-4-nitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=C(F)C=C1Cl CRONHBXGPYQWHX-UHFFFAOYSA-N 0.000 description 2
• CRXQYSQDOBKHNV-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound NC(=O)C1CCCC2=C1C1=C(OCC(O)=O)C=CC=C1N2CC1=CC=CC=C1 CRXQYSQDOBKHNV-UHFFFAOYSA-N 0.000 description 2
• RUTKJXMYXZFXPQ-UHFFFAOYSA-N 2-fluoro-5-methoxyaniline Chemical compound COC1=CC=C(F)C(N)=C1 RUTKJXMYXZFXPQ-UHFFFAOYSA-N 0.000 description 2
• WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
• JRQDVRIQJJPHEQ-UHFFFAOYSA-N 3970-35-2 Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1Cl JRQDVRIQJJPHEQ-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• MBOFGTOZLMXAMD-UHFFFAOYSA-N 9-(cyclopentylmethyl)-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1CCCC1 MBOFGTOZLMXAMD-UHFFFAOYSA-N 0.000 description 2
• SUCNZXOGTGJQOL-UHFFFAOYSA-N 9-[(2,6-dichlorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl SUCNZXOGTGJQOL-UHFFFAOYSA-N 0.000 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 description 2
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
• 238000007792 addition Methods 0.000 description 2
• 239000000538 analytical sample Substances 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 2
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
• VKCMWLOBUILIOQ-UHFFFAOYSA-N ethyl 3-bromo-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1=O VKCMWLOBUILIOQ-UHFFFAOYSA-N 0.000 description 2
• 239000012362 glacial acetic acid Substances 0.000 description 2
• 150000002500 ions Chemical class 0.000 description 2
• 125000000468 ketone group Chemical group 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 2
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
• JTLVTCUZWKZOKJ-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-1-chlorocarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=C(Cl)C=2N1CC1=CC=CC=C1 JTLVTCUZWKZOKJ-UHFFFAOYSA-N 0.000 description 2
• MHEOLKMEADRTLY-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=C(C)C=2N1CC1=CC=CC=C1 MHEOLKMEADRTLY-UHFFFAOYSA-N 0.000 description 2
• 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 2
• CKSUTZMEGFFIEN-UHFFFAOYSA-N methyl 2-[(9-benzyl-5-carbamoyl-1-methyl-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetate Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OCC(=O)OC)=CC=C(C)C=2N1CC1=CC=CC=C1 CKSUTZMEGFFIEN-UHFFFAOYSA-N 0.000 description 2
• DIUORHRTQPTEHA-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-(cyclohexylmethyl)carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1CCCCC1 DIUORHRTQPTEHA-UHFFFAOYSA-N 0.000 description 2
• CLVREPBFXISVON-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(3,5-dimethylphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC(C)=CC(C)=C1 CLVREPBFXISVON-UHFFFAOYSA-N 0.000 description 2
• LHOAGMPBVLOYLJ-UHFFFAOYSA-N methyl 2-bromo-3-[[3-oxo-5-[4-(trifluoromethyl)phenyl]cyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1Br LHOAGMPBVLOYLJ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• PCVLMLMVJMGCJV-UHFFFAOYSA-N methyl 5-hydroxy-9-(pyridin-2-ylmethyl)carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=N1 PCVLMLMVJMGCJV-UHFFFAOYSA-N 0.000 description 2
• YIEMRYNGKWONSK-UHFFFAOYSA-N methyl 5-hydroxy-9-(pyridin-3-ylmethyl)carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CN=C1 YIEMRYNGKWONSK-UHFFFAOYSA-N 0.000 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 description 2
• 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 description 2
• 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 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 description 2
• 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 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 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 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 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 description 2
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• 229930194542 Keto Natural products 0.000 description 1
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• UJYWHFKITZXBGA-UHFFFAOYSA-N N-benzyl-2-chloro-5-methoxyaniline ethyl 9-benzyl-8-chloro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylate Chemical compound C(C1=CC=CC=C1)NC1=C(C=CC(=C1)OC)Cl.C(C1=CC=CC=C1)N1C2=C(C=CC(=C2C=2C(CCCC12)C(=O)OCC)OC)Cl UJYWHFKITZXBGA-UHFFFAOYSA-N 0.000 description 1
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• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
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• 239000012298 atmosphere Substances 0.000 description 1
• JEHKKBHWRAXMCH-UHFFFAOYSA-M benzenesulfinate Chemical compound [O-]S(=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-M 0.000 description 1
• 150000003857 carboxamides Chemical class 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical class CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
• 239000002024 ethyl acetate extract Substances 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• 239000011888 foil Substances 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• UKXXOVPJZVIESK-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-(cyclopentylmethyl)carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1CCCC1 UKXXOVPJZVIESK-UHFFFAOYSA-N 0.000 description 1
• NFZUELIAEKCBJM-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-5-pentylcyclohexen-1-yl)amino]benzoate Chemical compound C1C(CCCCC)CC(=O)C=C1NC1=CC=CC(C(=O)OC)=C1Br NFZUELIAEKCBJM-UHFFFAOYSA-N 0.000 description 1
• PQWZEKJCTAZIQS-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-5-phenylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C=2C=CC=CC=2)=C1Br PQWZEKJCTAZIQS-UHFFFAOYSA-N 0.000 description 1
• REGWHUMRLZDXMW-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-5-propan-2-ylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C(C)C)=C1Br REGWHUMRLZDXMW-UHFFFAOYSA-N 0.000 description 1
• SRUQBVOXRAGPPX-UHFFFAOYSA-N methyl 2-bromo-3-[[5-(4-chlorophenyl)-3-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C=2C=CC(Cl)=CC=2)=C1Br SRUQBVOXRAGPPX-UHFFFAOYSA-N 0.000 description 1
• AWMFFKWRPSFLLU-UHFFFAOYSA-N methyl 2-bromo-3-[[5-(furan-2-yl)-3-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C=2OC=CC=2)=C1Br AWMFFKWRPSFLLU-UHFFFAOYSA-N 0.000 description 1
• ZJJOZUABJIVBLZ-UHFFFAOYSA-N methyl 2-bromo-3-[[5-(hydroxymethyl)-3-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CO)CC(=O)C=2)=C1Br ZJJOZUABJIVBLZ-UHFFFAOYSA-N 0.000 description 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 description 1
• VUJFIBWLMCQXKH-UHFFFAOYSA-N n-benzyl-2-chloro-5-methoxyaniline Chemical compound COC1=CC=C(Cl)C(NCC=2C=CC=CC=2)=C1 VUJFIBWLMCQXKH-UHFFFAOYSA-N 0.000 description 1
• 230000000802 nitrating effect Effects 0.000 description 1
• 239000004533 oil dispersion Substances 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 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
• 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
• 238000012746 preparative thin layer chromatography Methods 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
• JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
• KQOUGLLWYHJABD-UHFFFAOYSA-M sodium;2-(9-benzyl-5-carbamoyl-2-methoxycarbazol-4-yl)oxyacetate Chemical compound [Na+].C=1C(OC)=CC(OCC([O-])=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 KQOUGLLWYHJABD-UHFFFAOYSA-M 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
• QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• LHJCZOXMCGQVDQ-UHFFFAOYSA-N tri(propan-2-yl)silyl trifluoromethanesulfonate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F LHJCZOXMCGQVDQ-UHFFFAOYSA-N 0.000 description 1
• WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
• BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-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
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1