Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs

Eur J Med Chem. 2011 May;46(5):1463-72. doi: 10.1016/j.ejmech.2011.01.031. Epub 2011 Jan 28.

Abstract

A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 μg mL(-1). Compound 2a and 3a exhibited good activities against P. piricola at low dosage.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Drug Design*
  • Fungi / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry
  • Pyrroles / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Antifungal Agents
  • Pyrroles