LT4936B - Tricikliai poli(adp-ribozės) polimerazių inhibitoriai - Google Patents

Info

Publication number

LT4936B

LT4936B LT2001083A LT2001083A LT4936B LT 4936 B LT4936 B LT 4936B LT 2001083 A LT2001083 A LT 2001083A LT 2001083 A LT2001083 A LT 2001083A LT 4936 B LT4936 B LT 4936B

Authority

LT

Lithuania

Prior art keywords

mmol

compound

alkyl

pharmaceutically acceptable

tetrahydro

Prior art date

1999-01-11

Links

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• Global Dossier
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• 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 title claims description 71
• 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 title description 61
• 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 title description 61
• 239000003112 inhibitor Substances 0.000 title description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 132
• 230000000694 effects Effects 0.000 claims abstract description 22
• 239000003814 drug Substances 0.000 claims abstract description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 97
• 125000000217 alkyl group Chemical group 0.000 claims description 55
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 50
• -1 nitro, amino Chemical group 0.000 claims description 44
• 239000012453 solvate Substances 0.000 claims description 44
• 239000002207 metabolite Substances 0.000 claims description 40
• 239000000651 prodrug Substances 0.000 claims description 40
• 229940002612 prodrug Drugs 0.000 claims description 40
• 230000002401 inhibitory effect Effects 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000003342 alkenyl group Chemical group 0.000 claims description 29
• 239000003795 chemical substances by application Substances 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000000304 alkynyl group Chemical group 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 230000005764 inhibitory process Effects 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 102000004190 Enzymes Human genes 0.000 claims description 15
• 108090000790 Enzymes Proteins 0.000 claims description 15
• 231100000135 cytotoxicity Toxicity 0.000 claims description 14
• 230000003013 cytotoxicity Effects 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
• 238000003556 assay Methods 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 230000002255 enzymatic effect Effects 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 4
• 108010017601 Tankyrases Proteins 0.000 claims description 3
• 101710179684 Poly [ADP-ribose] polymerase Proteins 0.000 claims 15
• 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 claims 15
• 238000004519 manufacturing process Methods 0.000 claims 6
• 125000001475 halogen functional group Chemical group 0.000 claims 3
• 102100037664 Poly [ADP-ribose] polymerase tankyrase-1 Human genes 0.000 claims 2
• 238000011282 treatment Methods 0.000 abstract description 17
• 208000006011 Stroke Diseases 0.000 abstract description 10
• 230000004770 neurodegeneration Effects 0.000 abstract description 10
• 206010019196 Head injury Diseases 0.000 abstract description 9
• 208000015122 neurodegenerative disease Diseases 0.000 abstract description 9
• 229940127089 cytotoxic agent Drugs 0.000 abstract description 8
• 239000002254 cytotoxic agent Substances 0.000 abstract description 7
• 238000001959 radiotherapy Methods 0.000 abstract description 6
• 239000002246 antineoplastic agent Substances 0.000 abstract description 5
• 229940041181 antineoplastic drug Drugs 0.000 abstract description 4
• 206010028980 Neoplasm Diseases 0.000 abstract description 3
• 201000011510 cancer Diseases 0.000 abstract description 3
• 231100000599 cytotoxic agent Toxicity 0.000 abstract description 2
• 239000003558 transferase inhibitor Substances 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 301
• 239000007787 solid Substances 0.000 description 147
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 97
• 239000000243 solution Substances 0.000 description 97
• 229910052739 hydrogen Inorganic materials 0.000 description 95
• 238000004458 analytical method Methods 0.000 description 93
• 229910052799 carbon Inorganic materials 0.000 description 92
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 65
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 43
• JBXRLVPILRXPNH-UHFFFAOYSA-N indol-6-one Chemical compound O=C1C=CC2=CC=NC2=C1 JBXRLVPILRXPNH-UHFFFAOYSA-N 0.000 description 39
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 34
• 229940125797 compound 12 Drugs 0.000 description 34
• 235000002639 sodium chloride Nutrition 0.000 description 34
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
• 239000011541 reaction mixture Substances 0.000 description 32
• 238000000034 method Methods 0.000 description 29
• 239000011734 sodium Substances 0.000 description 27
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
• 239000010410 layer Substances 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 235000019439 ethyl acetate Nutrition 0.000 description 24
• 239000000203 mixture Substances 0.000 description 24
• 239000000543 intermediate Substances 0.000 description 22
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 241000124008 Mammalia Species 0.000 description 16
• 239000012043 crude product Substances 0.000 description 16
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 16
• 239000012267 brine Substances 0.000 description 15
• 238000004587 chromatography analysis Methods 0.000 description 15
• HCUARRIEZVDMPT-UHFFFAOYSA-N indolyl-2-carboxylic acid Natural products C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 15
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
• 239000012661 PARP inhibitor Substances 0.000 description 14
• 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 14
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 14
• WEAXQUBYRSEBJD-UHFFFAOYSA-N methyl 1h-indole-4-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1C=CN2 WEAXQUBYRSEBJD-UHFFFAOYSA-N 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 229910052763 palladium Inorganic materials 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 14
• 229910052786 argon Inorganic materials 0.000 description 13
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 12
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
• 238000001953 recrystallisation Methods 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000007864 aqueous solution Substances 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• 238000003818 flash chromatography Methods 0.000 description 11
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 11
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 150000001299 aldehydes Chemical class 0.000 description 9
• XYGKKJHGZOGVBL-UHFFFAOYSA-N azepan-3-one Chemical compound O=C1CCCCNC1 XYGKKJHGZOGVBL-UHFFFAOYSA-N 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 235000019198 oils Nutrition 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• 230000001225 therapeutic effect Effects 0.000 description 9
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• CETUIKOTKQSYEU-UHFFFAOYSA-N 2-iodo-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one Chemical compound O=C1NCCC2=C(I)NC3=CC=CC1=C32 CETUIKOTKQSYEU-UHFFFAOYSA-N 0.000 description 7
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 230000002829 reductive effect Effects 0.000 description 7
• 239000011592 zinc chloride Substances 0.000 description 7
• 235000005074 zinc chloride Nutrition 0.000 description 7
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
• DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 6
• ZRRIVOUCCUFNDH-UHFFFAOYSA-N 2-bromo-3,4,5,6-tetrahydro-azepino[5,4,3-cd]indol-6-one Chemical compound O=C1NCCC2=C(Br)NC3=CC=CC1=C32 ZRRIVOUCCUFNDH-UHFFFAOYSA-N 0.000 description 6
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
• 102000003960 Ligases Human genes 0.000 description 6
• 108090000364 Ligases Proteins 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• 206010029350 Neurotoxicity Diseases 0.000 description 6
• 108091026813 Poly(ADPribose) Proteins 0.000 description 6
• 206010044221 Toxic encephalopathy Diseases 0.000 description 6
• 125000005842 heteroatom Chemical group 0.000 description 6
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
• 230000007135 neurotoxicity Effects 0.000 description 6
• 231100000228 neurotoxicity Toxicity 0.000 description 6
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
• 125000003367 polycyclic group Chemical group 0.000 description 6
• 235000011056 potassium acetate Nutrition 0.000 description 6
• 230000003389 potentiating effect Effects 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 229910000029 sodium carbonate Inorganic materials 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 229960000303 topotecan Drugs 0.000 description 6
• AGPZUEDYVLUKMF-UHFFFAOYSA-N 1,3,4,5-tetrahydro-6h-azepino[5,4,3-cd]indol-6-one Chemical compound O=C1NCCC2=CNC3=CC=CC1=C23 AGPZUEDYVLUKMF-UHFFFAOYSA-N 0.000 description 5
• PYLXNOZFJZQGBX-UHFFFAOYSA-N 53462-75-2 Chemical compound C1=CC(C(=O)NC2)=C3C2=CNC3=C1 PYLXNOZFJZQGBX-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• 108020004414 DNA Proteins 0.000 description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 230000001404 mediated effect Effects 0.000 description 5
• CMCWXWQXFLAUFM-UHFFFAOYSA-N methyl 2-iodo-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1I CMCWXWQXFLAUFM-UHFFFAOYSA-N 0.000 description 5
• DIUAWEVAOAYVBP-UHFFFAOYSA-N molport-035-773-933 Chemical compound O=C1NCCC2=C(Br)NC3=CC(F)=CC1=C32 DIUAWEVAOAYVBP-UHFFFAOYSA-N 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 125000003107 substituted aryl group Chemical group 0.000 description 5
• NSYBOVGRQLCZSE-UHFFFAOYSA-N 1h-isoquinolin-5-one Chemical compound C1N=CC=C2C(=O)C=CC=C21 NSYBOVGRQLCZSE-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 230000032677 cell aging Effects 0.000 description 4
• 230000001413 cellular effect Effects 0.000 description 4
• 125000005843 halogen group Chemical group 0.000 description 4
• 230000004968 inflammatory condition Effects 0.000 description 4
• 229910052740 iodine Inorganic materials 0.000 description 4
• 230000005865 ionizing radiation Effects 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 229960004964 temozolomide Drugs 0.000 description 4
• 229910052725 zinc Inorganic materials 0.000 description 4
• 239000011701 zinc Substances 0.000 description 4
• VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 3
• BUWWUKGHOFKIPK-UHFFFAOYSA-N 12-phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one Chemical compound C=12C3=CNC2=CC=CC=1C(=O)NCC3C1=CC=CC=C1 BUWWUKGHOFKIPK-UHFFFAOYSA-N 0.000 description 3
• SUTWIDLKGDLRGV-UHFFFAOYSA-N 2-[4-(2-diethylamino-ethyl)-phenyl]-3,4,5,6-tetrahydro-azepino[5,4,3-cd]indol-6-one Chemical compound C1=CC(CCN(CC)CC)=CC=C1C(N1)=C2CCNC(=O)C3=C2C1=CC=C3 SUTWIDLKGDLRGV-UHFFFAOYSA-N 0.000 description 3
• CAFVDAIDYARFNM-UHFFFAOYSA-N 2-phenethyl-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NCCC2=C1CCC1=CC=CC=C1 CAFVDAIDYARFNM-UHFFFAOYSA-N 0.000 description 3
• CMVVSYUUFABRBC-UHFFFAOYSA-N 2-phenyl-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol-6-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NCCC2=C1C1=CC=CC=C1 CMVVSYUUFABRBC-UHFFFAOYSA-N 0.000 description 3
• XNFAEXRJJDIECW-UHFFFAOYSA-N 3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-9-one Chemical compound O=C1NN=CC2=CNC3=CC=CC1=C23 XNFAEXRJJDIECW-UHFFFAOYSA-N 0.000 description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
• BEZGOKXDSBWTEV-UHFFFAOYSA-N 6-oxo-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indole-2-carboxylic acid octyl ester Chemical compound O=C1NCCC2=C(C(=O)OCCCCCCCC)NC3=CC=CC1=C32 BEZGOKXDSBWTEV-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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