Novel spirooxindole-pyrrolidine compounds: synthesis, anticancer and molecular docking studies

Eur J Med Chem. 2014 Mar 3:74:50-64. doi: 10.1016/j.ejmech.2013.12.027. Epub 2014 Jan 3.

Abstract

Novel spirooxindole-pyrrolidine compounds have been synthesised through 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or thioproline with the dipolarophile 3-(1H-imidazol-2-yl)-2-(1H-indole-3-carbonyl)acrylonitrile under the optimised reaction condition. Synthesised compounds were evaluated for their anticancer activity against A549 human lung adenocarcinoma cancer cell line. Among the 29 tested compounds 4j, 6b and 6h showed very high activity 66.3%, 64.8% and 66.3% at 25 μg/mL concentration against A549 lung adenocarcinoma cancer cell line. These spirooxindole-pyrrolidine compounds can be promising therapeutic agents for A549 lung adenocarcinoma cancer cell line.

Keywords: Anticancer activity; Azomethine ylide cycloaddition; Molecular docking; Multicomponent reaction; Pyrrolidine; Spirooxindole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Humans
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Molecular Docking Simulation
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry*
  • Pyrrolidines / pharmacology

Substances

  • Antineoplastic Agents
  • Indoles
  • Pyrrolidines
  • pyrrolidine