The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid

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Article

Carballeira, Nestor M.¹  Miranda, Carlos¹  Parang, Keykavous² 

[1] Univ Puerto Rico, Dept Chem, San Juan, PR 00931 USA

[2] Univ Rhode Isl, Coll Pharm, Dept Biomed & Pharmaceut Sci, Kingston, RI 02881 USA

关键词: Antifungal;    Candida albicans;    Decanoic acid;    Methoxylated fatty acids;    Synthesis;   

DOI  :  10.1016/j.tetlet.2009.07.074

来源: Elsevier

【 摘 要 】

The hitherto unknown (+/-)-4-methoxydecanoic acid was synthesized in six steps and in 25% overall yield starting from commercially available 4-penten-1-ol. The title compound demonstrated 17-fold higher antifungal activity (MIC = 1.5 mu M) against Candida albicans ATCC 60193 and Cryptococcus neoformans ATCC 66031 when compared to unsubstituted n-decanoic acid. Our results demonstrate that mid-chain methoxylation appears to be a viable strategy for increasing the fungitoxicity of fatty acids. (C) 2009 Elsevier Ltd. All rights reserved.

【 授权许可】

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