A water mediated multicomponent reaction for the synthesis of novel spirooxindole derivatives and their antifungal activity

Org Biomol Chem. 2024 May 1;22(17):3459-3467. doi: 10.1039/d4ob00256c.

Abstract

A water mediated three-component reaction of isatin, 4-aminocoumarin, and 1,3-cyclodicarbonyl compounds is reported for the synthesis of spiro[chromeno[4,3-b]cyclopenta[e]pyridine-7,3'-indoline]trione and the spiro[chromeno[4,3-b]quinoline 7,3'-indoline]trione. Up to 27 different spirooxindole derivatives were synthesized by this method. The bioactivity of these spirooxindole derivatives was evaluated and they were found to show antifungal activity against Cercospora arachidicola, Physalospora piricola, Rhizoctonia cerealis, and Fusarium moniliforme.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents* / chemical synthesis
  • Antifungal Agents* / chemistry
  • Antifungal Agents* / pharmacology
  • Benzopyrans*
  • Fusarium / drug effects
  • Indoles* / chemical synthesis
  • Indoles* / chemistry
  • Indoles* / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nitriles*
  • Oxindoles / chemical synthesis
  • Oxindoles / chemistry
  • Oxindoles / pharmacology
  • Spiro Compounds* / chemical synthesis
  • Spiro Compounds* / chemistry
  • Spiro Compounds* / pharmacology
  • Structure-Activity Relationship
  • Water* / chemistry

Substances

  • Antifungal Agents
  • Spiro Compounds
  • Water
  • Indoles
  • Oxindoles
  • 2-oxindole
  • spirooxindole
  • Benzopyrans
  • Nitriles