Facile and diastereoselective synthesis of 3,2'-spiropyrrolidine-oxindoles derivatives, their molecular docking and antiproliferative activities

Bioorg Med Chem Lett. 2015 Jan 15;25(2):389-99. doi: 10.1016/j.bmcl.2014.10.099. Epub 2014 Nov 13.

Abstract

In the present study, a series of novel highly functionalized spiropyrrolidine-oxindoles have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide formed from isatin and various amino acids such as sarcosine, proline and thioproline with the dipolarophile (E)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-(1H-indole-3-carbonyl)acrylonitrile under optimized conditions. All the synthesized compounds were evaluated for their antimicrobial activity and shown significant activity.

Keywords: Antimicrobial activity; Molecular docking; Multicomponent reaction; Pyrazole moiety; Spirooxindole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / drug effects*
  • Cell Proliferation / drug effects*
  • Cells, Cultured
  • Humans
  • Indoles / chemistry*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Docking Simulation
  • Molecular Structure
  • Oxindoles
  • Pyrrolidines / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Indoles
  • Oxindoles
  • Pyrrolidines
  • Spiro Compounds
  • 2-oxindole