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Total Synthesis and Further Scrutiny of the in vitro Antifungal Activity of 6‐Nonadecynoic Acid
Author(s) -
Carballeira Néstor M.,
Sanabria David,
Parang Keykavous
Publication year - 2005
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200500102
Subject(s) - candida albicans , cryptococcus neoformans , antifungal , microbiology and biotechnology , fatty acid , corpus albicans , chemistry , in vitro , yield (engineering) , biochemistry , biology , materials science , metallurgy
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.