Facile synthesis of spirooxindole-pyrazolines and spirobenzofuranone-pyrazolines and their fungicidal activity

Org Biomol Chem. 2015 May 7;13(17):4869-78. doi: 10.1039/c5ob00258c.

Abstract

Novel spirooxindole-pyrazolines and spirobenzofuranone-pyrazolines have been synthesized in good to excellent yields via the annulation reactions of the corresponding 3-alkylideneoxindoles and 3-alkylidenebenzofuranones with Huisgen zwitterions. The preliminary bioassay demonstrated that some of the spiropyrazolines possess good in vitro fungicidal activity against several crop fungi at a concentration of 50 μg mL(-1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Benzofurans / chemical synthesis
  • Benzofurans / chemistry
  • Benzofurans / pharmacology*
  • Dose-Response Relationship, Drug
  • Fungi / drug effects*
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Oxindoles
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Benzofurans
  • Indoles
  • Oxindoles
  • Pyrazoles
  • Spiro Compounds
  • 2-oxindole