Synthesis and biological evaluation of 3-substituted-indolin-2-one derivatives containing chloropyrrole moieties

Molecules. 2011 Nov 8;16(11):9368-85. doi: 10.3390/molecules16119368.

Abstract

Eighteen novel 3-substituted-indolin-2-ones containing chloropyrroles were synthesized and their biological activities were evaluated. The presence of a chlorine atom on the pyrrole ring was crucial to reduce cardiotoxicity. The presence of a 2-(ethyl-amino)ethylcarbamoyl group as a substituent at the C-4' position of the pyrrole enhanced the antitumor activities notably. IC50 values as low as 0.32, 0.67, 1.19 and 1.22 μM were achieved against non-small cell lung cancer (A549), oral epithelial (KB), melanoma (K111) and large cell lung cancer cell lines (NCI-H460), respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor / drug effects
  • Chlorine / chemistry*
  • Drug Screening Assays, Antitumor
  • Humans
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Intercellular Signaling Peptides and Proteins / metabolism
  • Mice
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry*
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors

Substances

  • Antineoplastic Agents
  • Indoles
  • Intercellular Signaling Peptides and Proteins
  • Pyrroles
  • indolin-2-one
  • Chlorine
  • Vascular Endothelial Growth Factor Receptor-2