Direct synthesis of C3-mono-functionalized oxindoles from N-unprotected 2-oxindole and their antileishmanial activity

Bioorg Med Chem. 2014 Feb 1;22(3):1063-9. doi: 10.1016/j.bmc.2013.12.039. Epub 2013 Dec 25.

Abstract

A novel approach for the synthesis of unprecedented C3-mono-functionalized indolin-2-ones is reported, starting from 2-oxindole and chalcones. The reactions proceed regioselectively under mild conditions, without di- and tri-alkylated side products. The new compounds have been evaluated in vitro for their antiproliferative effects against the protozoan Leishmania infantum. Interestingly, they appear able to kill L. infantum promastigotes and amastigotes, without significant cytotoxic effects.

Keywords: Cyclization; Diastereoselectivity; Leishmania; Leishmanicidal activity; Michael addition; Oxindoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiprotozoal Agents / chemical synthesis
  • Antiprotozoal Agents / chemistry*
  • Antiprotozoal Agents / pharmacology*
  • Cell Line / drug effects
  • Chalcone
  • Chemistry Techniques, Synthetic
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical / methods
  • Indoles / chemistry*
  • Leishmania infantum / drug effects*
  • Mice
  • Oxindoles
  • Structure-Activity Relationship
  • Toxicity Tests

Substances

  • Antiprotozoal Agents
  • Indoles
  • Oxindoles
  • indolin-2-one
  • 2-oxindole
  • Chalcone