Discovery of novel c-Met kinase inhibitors bearing a thieno[2,3-d] pyrimidine or furo[2,3-d]pyrimidine scaffold

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 13, 2011, Pages 3906-3918

  Zhao, Ailing ^a   Gao, Xin ^a   Wang, Yuanxiang ^a   Ai, Jing ^a   Wang, Ying ^a   Chen, Yi ^a   Geng, Meiyu ^a   Zhang, Ao ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Antitumor; c Met; Furo 2,3 d pyrimidine; RTK; Thieno 2,3 d pyrimidine

Indexed keywords

2 AMINO 4 (4 FLUOROPHENYL)THIOPHENE 3 CARBONITRILE; 3 FLUORO 4 [5 (4 FLUOROPHENYL)THIENO[2,3 D]PYRIMIDIN 4 YLOXY]ANILINE; 4 CHLORO 5 (4 FLUOROPHENYL)THIENO[2,3 D]PYRIMIDINE; 5 (4 FLUOROPHENYL)THIENO[2,3 D]PYRIMIDIN 4(3H)ONE; FURO[2,3 D]PYRIMIDINE DERIVATIVE; N [3 FLUORO 4 (2 METHOXY 5 PHENYLFURO[2,3 D]PYRIMIDIN 4 YLOXY)PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 (2 METHYLTETRAHYDRO[1]BENZOTHIENO[2,3 D]PYRIMIDIN 4 YLOXY)PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 (5 METHYLFURO[2,3 D]PYRIMIDIN 4 YLOXY)PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 (5 PHENYLTHIENO[2,3 D]PYRIMIDIN 4 YLOXY)PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 (6 PHENYLTHIENO[2,3 D]PYRIMIDIN 4 YLOXY)PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 (6,7 DIHYDRO 5H CYCLOPENTAL[4,5]THIENO[2,3 D]PYRIMIDIN 4 YLOXY)PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 (6,7,8,9 TETRAHYDRO 5H CYCLOHEPTA[4,5]THIENO[2,3 D]PYRIMIDIN 4 YLOXY)PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [2 (METHYLAMINO) 5 PHENYLFURO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [2 (METHYLSULFONYL) 5 PHENYLFURO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [2 (METHYLTHIO) 5 PHENYLFURO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [2 METHYL 5 (THIOPHEN 2 YL)FURO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [5 (4 FLUOROPHENYL)THIENO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [5 (4 METHOXYPHENYL)THIENO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [5 (5 METHYLTHIOPHEN 2 YL)THIENO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [5 (NAPHTHALEN 2 YL)THIENO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [5 (THIOPHEN 2 YL)FURO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [3 FLUORO 4 [5 [4 (TRIFLUOROMETHYL)PHENYL]THIENO[2,3 D]PYRIMIDIN 4 YLOXY]PHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (2 AZIDO 5 PHENYLFURO[2,3 D]PYRIMIDIN 4 YLOXY) 3 FLUOROPHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 [5 (3,4 DIFLUOROPHENYL)THIENO[2,3 D]PYRIMIDIN 4 YLOXY] 3 FLUOROPHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 [5 (3,4 DIMETHOXYPHENYL)THIENO[2,3 D]PYRIMIDIN 4 YLOXY] 3 FLUOROPHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 [5 (BIPHENYL 4 YL)THIENO[2,3 D]PYRIMIDIN 4 YLOXY] 3 FLUOROPHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; PHOSPHOTRANSFERASE INHIBITOR; SCATTER FACTOR RECEPTOR; THIENO[2,3 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG EFFECT; DRUG HALF LIFE; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; GLIOBLASTOMA; HUMAN; HUMAN CELL; IC 50; NONHUMAN; SINGLE DRUG DOSE; TUMOR XENOGRAFT;

ANIMALS; CELL LINE, TUMOR; DRUG EVALUATION, PRECLINICAL; GLIOBLASTOMA; HUMANS; MICE; MICE, NUDE; PROTEIN KINASE INHIBITORS; PROTO-ONCOGENE PROTEINS C-MET; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; TRANSPLANTATION, HETEROLOGOUS;

EID: 79959518655     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.05.038     Document Type: Article

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