Receptor-guided 3D-QSAR approach for the discovery of c-kit tyrosine kinase inhibitors

J Mol Model. 2012 Jul;18(7):2885-95. doi: 10.1007/s00894-011-1304-0. Epub 2011 Nov 30.

Abstract

Studies of the the three-dimensional quantitative structure-activity relationships for ninety-five c-kit tyrosine kinase inhibitors were performed. Based on a co-crystallized compound (1 T46), known inhibitors were aligned with c-kit by induced-fit docking, and multiple training/test set splitting was performed to validate the selected pharmacophore model. The best pharmacophore model consisted of five features: one hydrogen-bond donor and four aromatic rings. Reliable statistics were obtained (R(2) = 0.95, R(pred) (2) = 0.75), and the model was validated by using it to select c-kit inhibitors from a database; 82.1% of the hits it retrieved were active. Accordingly, our model can be reliably used to identify new c-kit inhibitors, and can provide useful information when designing new inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Discovery
  • Models, Molecular*
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacology
  • Proto-Oncogene Proteins c-kit / antagonists & inhibitors
  • Proto-Oncogene Proteins c-kit / chemistry*
  • Quantitative Structure-Activity Relationship*

Substances

  • Protein Kinase Inhibitors
  • Proto-Oncogene Proteins c-kit