Efficient microwave enhanced regioselective synthesis of a series of benzimidazolyl/triazolyl spiro [indole-thiazolidinones] as potent antifungal agents and crystal structure of spiro[3H-indole-3,2'-thiazolidine]-3'(1,2,4-triazol-3-yl)-2,4'(1H)-dione

Bioorg Med Chem. 2006 Apr 1;14(7):2409-17. doi: 10.1016/j.bmc.2005.11.025.

Abstract

A microwave-assisted three-component, regioselective one-pot cyclocondensation method has been developed for the synthesis of a series of novel spiro[indole-thiazolidinones] (6a-l) using an environmentally benign procedure at atmospheric pressure in open vessel. This rapid method produces pure products in high yields within few minutes in comparison to a conventional two-step procedure. The crystal structure of one representative compound has been determined by X-ray diffraction. The synthesized compounds have been screened 'in vitro' for antifungal activity against Rhizoctonia solani, Fusarium oxysporum and Collectotrichum capsici. All compounds have shown good activity against these pathogens.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Benzimidazoles / chemistry*
  • Benzimidazoles / radiation effects
  • Colletotrichum / classification
  • Colletotrichum / drug effects
  • Crystallization
  • Fusarium / classification
  • Fusarium / drug effects
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacology
  • Indoles / radiation effects
  • Microwaves
  • Models, Molecular
  • Molecular Structure
  • Rhizoctonia / classification
  • Rhizoctonia / drug effects
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiazoles / chemistry
  • Thiazoles / radiation effects
  • Thiazolidines
  • Triazoles / chemistry*
  • Triazoles / radiation effects
  • X-Ray Diffraction

Substances

  • Antifungal Agents
  • Benzimidazoles
  • Indoles
  • Spiro Compounds
  • Thiazoles
  • Thiazolidines
  • Triazoles
  • spiro(3H-indole-3,2'-thiazolidine)-3'(1,2,4-triazol-3-yl)-2,4'(1H)-dione