Application of a novel [3+2] cycloaddition reaction to prepare substituted imidazoles and their use in the design of potent DFG-out allosteric B-Raf inhibitors

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 1, 2010, Pages 292-304

  Dietrich, Justin ^a   Gokhale, Vijay ^a   Wang, Xiadong ^a   Hurley, Laurence H ^a,b   Flynn, Gary A ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

Author keywords

Allosteric; B Raf; de novo; Kinase inhibitor; p38; Structure base design; Type II

Indexed keywords

2 TERT BUTYL N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 5 4 TOLYL 1H IMIDAZOLE 4 CARBOXAMIDE; 4 (3,4 DIFLUOROPHENYL)N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2 (TRIFLUOROMETHYL) 1H IMIDAZOLE 5 CARBOXAMIDE; 5 (3 CHLORO 4 FLUOROPHENYL) N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2 (TRIFLUOROMETHYL) 1H IMIDAZOLE 4 CARBOXAMIDE; 5 (3 FLUORO 4 METHYLPHENYL) N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2 (TRIFLUOROMETHYL) 1H IMIDAZOLE 4 CARBOXAMIDE; 5 (4 FLUORO 3 METHYLPHENYL) N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2 (TRIFLUOROMETHYL) 1H IMIDAZOLE 4 CARBOXAMIDE; 5 (4 FLUOROPHENYL) N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2 (TRIFLUOROMETHYL) 1H IMIDAZOLE 4 CARBOXAMIDE; B RAF KINASE; IMIDAZOLE DERIVATIVE; N [4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 5 4 TOLYL 2 (TRIFLUOROMETHYL) 1H IMIDAZOLE 4 CARBOXAMIDE; N [4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 5 PHENYL 2 (TRIFLUOROMETHYL) 1H IMIDAZOLE 4 CARBOXAMIDE; N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2 (TRIFLUOROMETHYL) 5 (3,4,5 TRIMETHOXYPHENYL) 1H IMIDAZOLE 4 CARBOXAMIDE; N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2 (TRIFLUOROMETHYL) 5 [2 (TRIFLUOROMETHYL)PHENYL] 1H IMIDAZOLE 4 CARBOXAMIDE; N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2 (TRIFLUOROMETHYL) 5 [3 (TRIFLUOROMETHYL)PHENYL] 1H IMIDAZOLE 4 CARBOXAMIDE; N[4 METHYL 3 (3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YLAMINO)PHENYL] 2,5 DIPHENYL 1H IMIDAZOLE 4 CARBOXAMIDE; PROTEIN SERINE THREONINE KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS;

ANIMALS; CYCLIZATION; HUMANS; IMIDAZOLES; MICE; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; PROTO-ONCOGENE PROTEINS B-RAF;

EID: 72049094773     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.10.055     Document Type: Article

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