SE509700C2 - Nya isoindolderivat och salter därav, förfaranden för framställning därav samt anti-tumörmedel som innehåller dem - Google Patents

Info

Publication number

SE509700C2

SE509700C2 SE9003476A SE9003476A SE509700C2 SE 509700 C2 SE509700 C2 SE 509700C2 SE 9003476 A SE9003476 A SE 9003476A SE 9003476 A SE9003476 A SE 9003476A SE 509700 C2 SE509700 C2 SE 509700C2

Authority

SE

Sweden

Prior art keywords

group

compound

general formula

unsubstituted

dicarboximide

Prior art date

1989-11-01

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• 150000003839 salts Chemical class 0.000 title claims abstract description 41
• 238000000034 method Methods 0.000 title claims description 59
• 238000002360 preparation method Methods 0.000 title claims description 41
• 230000008569 process Effects 0.000 title claims description 13
• 125000000904 isoindolyl group Chemical class C=1(NC=C2C=CC=CC12)* 0.000 title abstract description 4
• 239000002246 antineoplastic agent Substances 0.000 title description 8
• 230000000259 anti-tumor effect Effects 0.000 claims abstract description 7
• 150000001875 compounds Chemical class 0.000 claims description 338
• 239000000203 mixture Substances 0.000 claims description 140
• -1 methylenedioxy groups Chemical group 0.000 claims description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• 150000002518 isoindoles Chemical class 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000002252 acyl group Chemical group 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 4
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000005270 trialkylamine group Chemical group 0.000 claims description 4
• NCPXNZOMQGQMFI-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-9-hydroxy-5-methoxy-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C1=C(O)C=C2C3=C(C(N(CCN(CC)CC)C4=O)=O)C4=CC(OC)=C3NC2=C1 NCPXNZOMQGQMFI-UHFFFAOYSA-N 0.000 claims description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• FEEAXBRLSNHURH-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-9-hydroxy-5-methyl-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C1=C(O)C=C2C3=C(C(N(CCN(C)C)C4=O)=O)C4=CC(C)=C3NC2=C1 FEEAXBRLSNHURH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims 8
• 239000004480 active ingredient Substances 0.000 claims 2
• JTPUOHDINRMSJM-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-9-hydroxy-5-methyl-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C1=C(O)C=C2C3=C(C(N(CCN(CC)CC)C4=O)=O)C4=CC(C)=C3NC2=C1 JTPUOHDINRMSJM-UHFFFAOYSA-N 0.000 claims 1
• SRXFLGPRBHGSCF-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-9-hydroxy-5-(2-methylcyclopropyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group CN(CCN1C(=O)C=2C=C(C=3NC4=CC=C(C=C4C=3C=2C1=O)O)C1C(C1)C)C SRXFLGPRBHGSCF-UHFFFAOYSA-N 0.000 claims 1
• MKGIUIUSQGCRKM-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-9-hydroxy-5-phenoxy-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C=12NC3=CC=C(O)C=C3C2=C2C(=O)N(CCN(C)C)C(=O)C2=CC=1OC1=CC=CC=C1 MKGIUIUSQGCRKM-UHFFFAOYSA-N 0.000 claims 1
• SYLCTHKSMSSLDS-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-9-hydroxy-5-phenyl-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C=12NC3=CC=C(O)C=C3C2=C2C(=O)N(CCN(C)C)C(=O)C2=CC=1C1=CC=CC=C1 SYLCTHKSMSSLDS-UHFFFAOYSA-N 0.000 claims 1
• DQHYLAALUXFRQZ-UHFFFAOYSA-N 2-[2-(ethylamino)ethyl]-9-hydroxy-5-methyl-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C1=C(O)C=C2C3=C(C(N(CCNCC)C4=O)=O)C4=CC(C)=C3NC2=C1 DQHYLAALUXFRQZ-UHFFFAOYSA-N 0.000 claims 1
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
• PBKUWQWAECCLHW-UHFFFAOYSA-N 5-chloro-2-[2-(dimethylamino)ethyl]-9-hydroxy-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C1=C(O)C=C2C3=C(C(N(CCN(C)C)C4=O)=O)C4=CC(Cl)=C3NC2=C1 PBKUWQWAECCLHW-UHFFFAOYSA-N 0.000 claims 1
• LCUWEOZAXJTOMT-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(dimethylamino)ethyl]-9-hydroxy-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C=12NC3=CC=C(O)C=C3C2=C2C(=O)N(CCN(C)C)C(=O)C2=CC=1C1CCC1 LCUWEOZAXJTOMT-UHFFFAOYSA-N 0.000 claims 1
• IFCBVJSMOOZNBG-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(dimethylamino)ethyl]-9-hydroxy-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C=12NC3=CC=C(O)C=C3C2=C2C(=O)N(CCN(C)C)C(=O)C2=CC=1C1CC1 IFCBVJSMOOZNBG-UHFFFAOYSA-N 0.000 claims 1
• IFGAXUMIPJUCFP-UHFFFAOYSA-N 9-hydroxy-5-methyl-2-[2-(methylamino)ethyl]-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical group C1=C(O)C=C2C3=C(C(N(CCNC)C4=O)=O)C4=CC(C)=C3NC2=C1 IFGAXUMIPJUCFP-UHFFFAOYSA-N 0.000 claims 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
• 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
• 229940124597 therapeutic agent Drugs 0.000 claims 1
• 125000005208 trialkylammonium group Chemical group 0.000 claims 1
• 231100000053 low toxicity Toxicity 0.000 abstract description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
• 239000000243 solution Substances 0.000 description 114
• 239000002904 solvent Substances 0.000 description 98
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 89
• 230000002829 reductive effect Effects 0.000 description 85
• 238000004821 distillation Methods 0.000 description 75
• 238000006243 chemical reaction Methods 0.000 description 65
• 239000013078 crystal Substances 0.000 description 55
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 47
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 47
• 125000001424 substituent group Chemical group 0.000 description 47
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 43
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• 239000012044 organic layer Substances 0.000 description 33
• 238000004440 column chromatography Methods 0.000 description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• 239000003480 eluent Substances 0.000 description 30
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• 238000001914 filtration Methods 0.000 description 26
• 238000002844 melting Methods 0.000 description 26
• 230000008018 melting Effects 0.000 description 26
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
• 238000003756 stirring Methods 0.000 description 17
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000000463 material Substances 0.000 description 15
• 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 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• 239000002198 insoluble material Substances 0.000 description 12
• 239000011541 reaction mixture Substances 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 11
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 10
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 241000699670 Mus sp. Species 0.000 description 8
• 230000002411 adverse Effects 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 8
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
• 230000000704 physical effect Effects 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 238000001953 recrystallisation Methods 0.000 description 8
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 239000008096 xylene Substances 0.000 description 7
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• 206010028980 Neoplasm Diseases 0.000 description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
• 150000008282 halocarbons Chemical class 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 101100020289 Xenopus laevis koza gene Proteins 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 238000006356 dehydrogenation reaction Methods 0.000 description 5
• 239000007789 gas Substances 0.000 description 5
• 239000008103 glucose Substances 0.000 description 5
• 125000001041 indolyl group Chemical group 0.000 description 5
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
• WBOJHPKCSKXRLN-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical compound C1=CC=C2C3=C(C(N(CCN(C)C)C4=O)=O)C4=CC=C3NC2=C1 WBOJHPKCSKXRLN-UHFFFAOYSA-N 0.000 description 4
• RZMIKXRWHRCZMI-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-7,8,9,10-tetrahydro-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical compound C1CCCC2=C1NC1=CC=C3C(=O)N(CCN(C)C)C(=O)C3=C12 RZMIKXRWHRCZMI-UHFFFAOYSA-N 0.000 description 4
• VDMKGLWVNFFPMX-UHFFFAOYSA-N 2-benzyl-4,5,6,10c-tetrahydro-3ah-pyrrolo[3,4-c]carbazole-1,3-dione Chemical compound O=C1C2CCC=3NC4=CC=CC=C4C=3C2C(=O)N1CC1=CC=CC=C1 VDMKGLWVNFFPMX-UHFFFAOYSA-N 0.000 description 4
• WOZVNQGWQGBXFG-UHFFFAOYSA-N 2-benzyl-6h-pyrrolo[3,4-c]carbazole-1,3-dione Chemical compound O=C1C(C=2C3=CC=CC=C3NC=2C=C2)=C2C(=O)N1CC1=CC=CC=C1 WOZVNQGWQGBXFG-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 150000001408 amides Chemical class 0.000 description 4
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 4
• 238000006053 organic reaction Methods 0.000 description 4
• 238000007254 oxidation reaction Methods 0.000 description 4
• 229910052760 oxygen Inorganic materials 0.000 description 4
• 239000001301 oxygen Substances 0.000 description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 238000006467 substitution reaction Methods 0.000 description 4
• 230000004083 survival effect Effects 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
• LHIBRDDXUMZVNS-UHFFFAOYSA-N 1-methyl-2-prop-1-en-2-ylindole Chemical compound C1=CC=C2N(C)C(C(=C)C)=CC2=C1 LHIBRDDXUMZVNS-UHFFFAOYSA-N 0.000 description 3
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