Design, synthesis, and evaluation of 5-methyl-4-phenoxy-5H-pyrrolo[3,2-d] pyrimidine derivatives: Novel VEGFR2 kinase inhibitors binding to inactive kinase conformation

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 20, 2010, Pages 7260-7273

  Oguro, Yuya ^a   Miyamoto, Naoki ^a   Okada, Kengo ^a   Takagi, Terufumi ^a   Iwata, Hidehisa ^a   Awazu, Yoshiko ^a   Miki, Hiroshi ^a   Hori, Akira ^a   Kamiyama, Keiji ^a   Imamura, Shinichi ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

Diphenylurea; Pyrrolo 3,2 d pyrimidine; Type II inhibitor; VEGFR

Indexed keywords

1 (2 CHLOROPHENYL) 3 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]UREA; 1 (3 BROMOPHENYL) 3 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]UREA; 1 (3 CHLOROPHENYL) 3 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]UREA; 1 (3 FLUOROPHENYL) 3 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]UREA; 1 (3 METHYLPHENYL) 3 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]UREA; 1 (4 CHLOROPHENYL) 3 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]UREA; 1 [2 CHLORO 4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 [3 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [2 FLUORO 4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 [3 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [2 METHOXY 4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 [3 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [3 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 PHENYLUREA; 1 [3 CHLORO 4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 [3 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)AMINO]PHENYL] 3 PHENYLUREA; 1 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 [3 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 PHENYLTHIOUREA; 1 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 PHENYLUREA; 1 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 3 PROPYLUREA; 1 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)SULFANYL]PHENYL] 3 PHENYLUREA; 1 [4 [METHYL (5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)AMINO]PHENYL] 3 [3 (TRIFLUOROMETHYL)PHENYL]UREA; 1 METHYL 3 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]UREA; 2 [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] N PHENYLACETAMIDE; 3 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY] N PHENYLBENZAMIDE; 4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY] N PHENYLBENZAMIDE; 5 METHYL 4 PHENOXY 5H PYRROLO [3,2 D]PYRIMIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; N [3 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]BENZAMIDE; N [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 1H BENZIMIDAZOL 2 AMINE; N [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL] 2 PHENYLACETAMIDE; N [4 [(5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 4 YL)OXY]PHENYL]BENZAMIDE; PROTEIN TYROSINE KINASE INHIBITOR; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 2;

ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; CANCER CELL; CANCER INHIBITION; CELL PROLIFERATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG BLOOD LEVEL; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENDOTHELIUM CELL; ENZYME INHIBITION; HUMAN; HUMAN CELL; MALE; MOUSE; NONHUMAN; PROSTATE CANCER; STRUCTURE ACTIVITY RELATION; UMBILICAL VEIN;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; BINDING SITES; CELLS, CULTURED; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HUMANS; MICE; MICE, NUDE; PHENYLUREA COMPOUNDS; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; PROTEIN STRUCTURE, TERTIARY; PYRIMIDINES; PYRROLES; RECEPTOR, TIE-2; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-2; XENOGRAFT MODEL ANTITUMOR ASSAYS;

MUS MUSCULUS;

EID: 77957595999     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.08.017     Document Type: Article

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