3,4-Disubstituted isothiazoles: novel potent inhibitors of VEGF receptors 1 and 2

Bioorg Med Chem Lett. 2009 Feb 15;19(4):1195-8. doi: 10.1016/j.bmcl.2008.12.078. Epub 2008 Dec 24.

Abstract

Novel derivatives of isothiazoles are described as potent ATP-competitive inhibitors of vascular endothelial growth factor receptors I and II (VEGFR-1/2). A number of compounds exhibited VEGFR-2 inhibitory activity comparable to that of Vatalanib in both HTRF enzymatic and cellular assays. Several derivatives featuring bulky meta-substituents in the amide portion of the molecule displayed 4- to 8-fold specificity for VEGFR-2 versus VEGFR-1. Active molecules also showed high intrinsic permeability (> 30 x 10(-5) cm/min) across Caco-2 cell monolayer.

MeSH terms

  • Adenosine Triphosphate / metabolism
  • Caco-2 Cells
  • Combinatorial Chemistry Techniques
  • Drug Design
  • Humans
  • Indoles / pharmacology
  • Molecular Structure
  • Niacinamide / analogs & derivatives
  • Niacinamide / pharmacology
  • Oligonucleotides
  • Phthalazines / pharmacology
  • Pyridines / pharmacology
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*
  • Vascular Endothelial Growth Factor Receptor-1 / antagonists & inhibitors*
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*

Substances

  • Indoles
  • Oligonucleotides
  • Phthalazines
  • Pyridines
  • Thiazoles
  • Niacinamide
  • vatalanib
  • Adenosine Triphosphate
  • Vascular Endothelial Growth Factor Receptor-1
  • Vascular Endothelial Growth Factor Receptor-2
  • imetelstat