Design, synthesis, biological evaluation and X-ray crystal structure of novel classical 6,5,6-tricyclic benzo[4,5]thieno[2,3-d]pyrimidines as dual thymidylate synthase and dihydrofolate reductase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 11, 2011, Pages 3585-3594

  Zhang, Xin ^a   Zhou, Xilin ^a   Kisliuk, Roy L ^b   Piraino, Jennifer ^c   Cody, Vivian ^c   Gangjee, Aleem ^a  

^a DUQUESNE UNIVERSITY   (United States)

^b Boston University Medical Campus   (United States)

^c HAUPTMAN WOODWARD MEDICAL RESEARCH INSTITUTE   (United States)

Author keywords

DHFR; Dual; Inhibitor; TS

Indexed keywords

2 [5 [[(2 AMINO 4 OXO 3,4 DIHYDRO[1]BENZOTHIENO[2,3,D]PYRIMIDIN 5 YL)METHYL]AMINO] 1 OXO 1,3 DIHYDRO 2H ISOINDOL 2 YL]PENTANEDIOIC ACID; 2 [5 [[(2 METHYL 4 OXO 3,4 DIHYDRO[1]BENZOTHIENO[2,3,D]PYRIMIDIN 5 YL)METHYL]AMINO] 1 OXO 1,3 DIHYDRO 2H ISOINDOL 2 YL]PENTANEDIOIC ACID; 2 AMINO 5 METHYL 5,6,7,8 TETRAHYDRO[1]BENZOTHIENO[2,3,D]PYRIMIDIN 4(3H) ONE; 2 AMINO 5 METHYL[1]BENZOTHIENO[2,3,D]PYRIMIDIN 4(3H) ONE; 2,2 DIMETHYL N (5 METHYL 4 OXO 3,4 DIHYDRO[1]BENZOTHIENO[2,3,D]PYRIMIDIN 2 YL)PROPANAMIDE; 2,2 DIMETHYL N (5 METHYL 4 OXO 3,4,5,6,7,8 HEXAHYDRO[1]BENZOTHIENO[2,3,D]PYRIMIDIN 2 YL)PROPANAMIDE; 2,5 DIMETHYL[1]BENZOTHIENO[2,3,D]PYRIMIDIN 4(3H) ONE; 5 (BROMOMETHYL) 2 METHYL[1]BENZOTHIENO[2,3,D]PYRIMIDIN 4(3H) ONE; 6,5,6 TRICYCLIC BENZO[4,5]THIENO[2,3,D]PYRIMIDINE; DIETHYL 2 (5 AMINO 1 OXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)PENTANEDIOIC ACID; DIETHYL 2 (5 NITRO 1 OXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)PENTANEDIOIC ACID; ETHYL 2 AMINO 4 METHYL 1 BENZOTHIOPHENE 3 CARBOXYLIC ACID; ETHYL 2 AMINO 4 METHYL 4,5,6,7 TETRAHYDRO 1 BENZOTHIOPHENE 3 CARBOXYLIC ACID; FOLIC ACID ANTAGONIST; METHYL 2 (BROMOMETHYL) 4 NITROBENZOIC ACID; METHYL 2 METHYL 4 NITROBENZOIC ACID; N [4 [[(2 METHYL 4 OXO 3,4 DIHYDRO[1]BENZOTHIENO[2,3,D]PYRIMIDIN 5 YL)METHYL]AMINO]BENZOYL]GLUTAMIC ACID; OXIDOREDUCTASE INHIBITOR; THYMIDYLATE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BIOLOGICAL ACTIVITY; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG BINDING; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IC 50; NONHUMAN; OXIDATION; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; FOLIC ACID ANTAGONISTS; HUMANS; MOLECULAR CONFORMATION; PYRIMIDINES; TETRAHYDROFOLATE DEHYDROGENASE; THYMIDYLATE SYNTHASE;

EID: 79957473801     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.067     Document Type: Article

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