4-((2-((4-Chloro-3-((((2S)-1-methyl-2-pyrrolidinyl)methyl)oxy)-phenyl)amino)-1,3-benzoxazol-5-yl)oxy)-N-methyl-2-pyridinecarboxamide

IC50 = 28 nM

OTAVAchemicals Catalogue Number: 1156358

CAS Registry Number: 769960-39-6

Purity: 95%+ (HPLC)

Ref.: Potashman, M. H., Bready, J., Coxon, A., DeMelfi,, T. M., DiPietro, L., Doerr, N., … Zhao, H. (2007). Design, Synthesis, and Evaluation of Orally Active Benzimidazoles and Benzoxazoles as Vascular End othelial Growth Factor-2 Receptor Tyrosine Kinase Inhibitors. Journal of Medicinal Chemistry, 50(18), 4351–4373.

Abstract: Inhibition of the VEGF signaling pathway has become a valuable approach in the treatment of cancers. Guided by X-ray crystallography and molecular modeling, a series of 2-aminobenzimidazoles and 2-aminobenzoxazoles were identified as potent inhibitors of VEGFR-2 (KDR) in both enzymatic and HUVEC cellular proliferation assays. In this report we describe the synthesis and structure-activity relationship of a series of 2-aminobenzimidazoles and benzoxazoles, culminating in the identification of benzoxazole 22 as a potent and selective VEGFR-2 inhibitor displaying a good pharmacokinetic profile. Compound 22 demonstrated efficacy in both the murine matrigel model for vascular permeability (79% inhibition observed at 100 mg/kg) and the rat corneal angiogenesis model (ED50 ) 16.3 mg/kg).

DOI: 10.1021/jm070034i

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