Biphenyl derivatives incorporating urea unit as novel VEGFR-2 inhibitors: design, synthesis and biological evaluation

Bioorg Med Chem. 2014 Jan 1;22(1):277-84. doi: 10.1016/j.bmc.2013.11.027. Epub 2013 Nov 21.

Abstract

A series of novel biphenyl urea derivates were synthesized and investigated for their potential to inhibit vascular endothelial growth factor receptor-2 (VEGFR-2). In particular, A7, B3 and B4 displayed significant enzymatic inhibitory activities, with IC₅₀ values of 4.06, 4.55 and 5.26 nM. Compound A7 exhibited potent antiproliferative activity on several cell lines. SAR study suggested that the introduction of methyl at ortho-position of the biphenyl urea and tertiary amine moiety could improve VEGFR-2 inhibitory activity and antitumor effects. Molecular docking indicated that the urea moiety formed four hydrogen bonds with DFG residue. These biphenyl ureas could serve as promising lead compounds for further optimization.

Keywords: Angiogenesis; Biphenyl scaffold; Urea moiety; VEGFR-2 inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds / chemistry
  • Cell Proliferation
  • Humans
  • Models, Molecular
  • Neovascularization, Pathologic
  • Urea / analogs & derivatives
  • Urea / chemical synthesis*
  • Urea / pharmacology
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*
  • Vascular Endothelial Growth Factor Receptor-2 / metabolism

Substances

  • Biphenyl Compounds
  • diphenyl
  • Urea
  • Vascular Endothelial Growth Factor Receptor-2