Carballeira Néstor M, Miranda Carlos, Parang Keykavous
Department of Chemistry, University of Puerto Rico, Rio Piedras campus, PO BOX 23346, San Juan, Puerto Rico 00931.
Tetrahedron Lett. 2009 Oct 14;50(41):5699-5700. doi: 10.1016/j.tetlet.2009.07.074.
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 seventeen fold higher antifungal activity (MIC = 1.5 mM) 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.
从市售的4-戊烯-1-醇出发，通过六步反应合成了此前未知的（±）-4-甲氧基癸酸，总产率为25%。与未取代的正癸酸相比，标题化合物对白色念珠菌ATCC 60193和新型隐球菌ATCC 66031的抗真菌活性高17倍（MIC = 1.5 mM）。我们的结果表明，中链甲氧基化似乎是提高脂肪酸杀真菌毒性的一种可行策略。
