Itraconazole Side Chain Analogues: Structure-Activity Relationship Studies for Inhibition of Endothelial Cell Proliferation, Vascular Endothelial Growth Factor Receptor 2 (VEGFR2) Glycosylation, and Hedgehog Signaling

Journal of Medicinal Chemistry

Volumn 54, Issue 20, 2011, Pages 7363-7374

  Shi, Wei ^a   Nacev, Benjamin A ^a   Aftab, Blake T ^a   Head, Sarah ^a   Rudin, Charles M ^a   Liu, Jun O ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (1 CYCLOHEXYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (1 CYCLOPENTYLMETHYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (1 ETHYLPROPYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (1 METHYLBUTYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (3 METHYLBUTYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (5 CYANOPENTYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (6 PHENYLHEXYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (HEX 3 YNYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 (N OCTYL) 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 [(3 ETHYLOXETAN 3 YL)METHYL] 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 [2 (3 METHYL 3H DIAZIRIN 3 YL)ETHYL] 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 [7 (3 METHYL 3H DIAZIRIN-3 YL)HEPTYL] 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 BUTYL 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 ETHYL 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 ISOBUTYL 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 ISOPROPYL 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 METHYL 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 PENTYL 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO 2 PROPYL 3H 1,2,4 TRIAZOL 3 ONE; 4 [4 [4 [4 [[2 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL L YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY]PHENYL]PIPERAZINYL]PHENYL] 2,4 DIHYDRO-2 (3 METHYLBUTYL) 3H 1,2,4 TRIAZOL 3 ONE; ITRACONAZOLE; SONIC HEDGEHOG PROTEIN; TRANSCRIPTION FACTOR GLI1; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 2;

ANIMAL CELL; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENDOTHELIUM CELL; GLYCOSYLATION; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

ANGIOGENESIS INHIBITORS; ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; ENDOTHELIAL CELLS; GLYCOSYLATION; HEDGEHOG PROTEINS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; ITRACONAZOLE; MICE; ONCOGENE PROTEINS; SIGNAL TRANSDUCTION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRANS-ACTIVATORS; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-2;

EID: 80054949042     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200944b     Document Type: Article

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