Synthesis and antifungal activities of myristic acid analogs

Keykavous Parang, Edward E. Knaus, Leonard I. Wiebe, Soroush Sardari, Mohsen Daneshtalab, Ferenc Csizmadia

Research output: Contribution to journalArticlepeer-review

Abstract

Myristic acid analogs that are putative inhibitors of N-myristoyl transferase were tested in vitro for activity against yeasts (Saccharomyces cerevisiae, Candida albicans, Cryptococcus neoformans) and filamentous fungi (Aspergillus niger). Several (±)-2-halotetradecanoic acids including (±)-2-bromotetradecanoic acid (14c) exhibited potent activity against C. albicans (MIC = 39 μM), C. neoformans (MIC = 20 μM), S. cerevisiae (MIC = 10 μM), and A. niger (MIC <42 μM) in RPMI 1640 media. Improved synthetic methods have been developed for the synthesis of 12-fluorododecanoic acid (12a) and 12-chlorododecanoic acid (12c). Three novel fatty acids, 12-chloro-4-oxadodecanoic acid (8a), 12-phenoxydodecanoic acid (12i), and 11-(4-iodophenoxy)-undecanoic acid (13d) were also synthesized and tested.

Original languageEnglish (US)
Pages (from-to)475-482
Number of pages8
JournalArchiv der Pharmazie
Volume329
Issue number11
StatePublished - Nov 1996
Externally publishedYes

Keywords

  • antifungal activity
  • myristic acid
  • myristoyl CoA:protein N-myristoyltransferase (NMT)
  • structure-activity relationships

ASJC Scopus subject areas

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

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