Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamides

Eur J Med Chem. 2009 Jul;44(7):2782-6. doi: 10.1016/j.ejmech.2009.01.012. Epub 2009 Jan 22.

Abstract

A series of cyclopropanecarboxamide were prepared and tested for antifungal activity in vivo. The preliminary bioassays indicated that some compounds are comparable to the commercial fungicides. To further explore the comprehensive structure-activity relationship on the basis of fungicidal activity data, comparative molecular field analysis (CoMFA) was performed, and a statistically reliable model with good predictive power (r(2)=0.8, q(2)=0.516) was achieved. Based on the CoMFA, compound 7p was designed and synthesized, which was found to display a good antifungal activity (79.38%) as 7g and 7h.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Cyclopropanes / chemical synthesis
  • Cyclopropanes / chemistry*
  • Cyclopropanes / pharmacology*
  • Fungi / drug effects*
  • Models, Molecular
  • Molecular Conformation
  • Quantitative Structure-Activity Relationship*

Substances

  • Amides
  • Antifungal Agents
  • Cyclopropanes
  • cyclopropanecarboxamide