Total synthesis and further scrutiny of the in vitro antifungal activity of 6-nonadecynoic acid

Néstor M. Carballeira, David Sanabria, Keykavous Parang

Research output: Contribution to journalArticlepeer-review

Abstract

The antifungal, naturally occurring acetylenic fatty acid 6-nonadecynoic acid was synthesized in three steps (18% overall yield), for the first time starting with commercially available 1-tetradecyne. The synthesis developed herein will facilitate the further study of the antifungal properties of this naturally occurring acetylenic fatty acid. The 6-nonadecynoic acid exhibited the best antifungal activity (<4.3 μM) against Cryptococcus neoformans ATCC 66031 in Sabouraud Dextrose Broth (SDB) media. In our hands, it was not active against Candida albicans ATCC 14053 and Candida albicans ATCC 60193.

Original languageEnglish (US)
Pages (from-to)441-443
Number of pages3
JournalArchiv der Pharmazie
Volume338
Issue number9
DOIs
StatePublished - Sep 2005
Externally publishedYes

Keywords

  • Acetylenic acids
  • Antifungal
  • C. neoformans
  • Fatty acids
  • Synthesis

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

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