Design, synthesis and biological evaluation of pyrazolyl-nitroimidazole derivatives as potential EGFR/HER-2 kinase inhibitors

Bioorg Med Chem Lett. 2016 Jan 15;26(2):677-683. doi: 10.1016/j.bmcl.2015.11.040. Epub 2015 Nov 14.

Abstract

A series of novel pyrazole-nitroimidazole derivatives had been arranged and evaluated for their EGFR/HER-2 tyrosine kinase inhibitory activity as well as their antiproliferative properties on four kinds of cancer cell lines (MCF-7, Hela, HepG2, B16-F10). The bioassay results showed most of the designed compounds exhibited potential antiproliferation activity, with the IC50 values ranging from 0.13μM to 128.06μM in four tumor cell lines. Among them, compound 5c exhibited remarkable inhibitory activity against EGFR/HER-2 tyrosine kinase with IC50 value of 0.26μM/0.51μM, respectively, comparable to the positive control erlotinib (IC50=0.41μM for HER-2 and IC50=0.20μM for EGFR) and lapatinib (IC50=0.54μM for HER-2 and IC50=0.28μM for EGFR). Molecular modeling simulation studies were performed in order to predict the biological activity of the proposed compounds and activity relationship (SAR) of these pyrazole-nitroimidazole derivatives.

Keywords: Anticancer activity; Cytotoxicity; EGFR/HER-2 inhibitors; Molecular docking and QSAR; Pyrazole-nitroimidazole derivatives.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design
  • ErbB Receptors / antagonists & inhibitors*
  • ErbB Receptors / metabolism
  • Humans
  • Molecular Docking Simulation
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Nitroimidazoles / chemistry*
  • Nitroimidazoles / pharmacology*
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacology*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Receptor, ErbB-2 / antagonists & inhibitors*
  • Receptor, ErbB-2 / metabolism

Substances

  • Antineoplastic Agents
  • Nitroimidazoles
  • Protein Kinase Inhibitors
  • Pyrazoles
  • EGFR protein, human
  • ERBB2 protein, human
  • ErbB Receptors
  • Receptor, ErbB-2