ArticleChemistry and physics of lipids2011
First total synthesis and antileishmanial activity of (Z)-16-methyl-11-heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata.
Article in Chemistry and physics of lipids, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed, 14 citations in OpenAlex.
- Rhodium-Catalyzed Anti-Markovnikov Transfer Hydroiodination of Terminal Alkynes.Angewandte Chemie (International ed. in English) · 2023Article
- Potential therapeutic targets shared between leishmaniasis and cancer.Parasitology · 2021Review
- Screening Marine Natural Products for New Drug Leads against Trypanosomatids and Malaria.Marine drugs · 2020Review
- Recent developments in drug discovery for leishmaniasis and human African trypanosomiasis.Chemical reviews · 2014Review
- Article
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
The first total synthesis for the (Z)-16-methyl-11-heptadecenoic acid, a novel fatty acid from the sponge Dragmaxia undata, was accomplished in seven steps and in a 44% overall yield. The use of (trimethylsilyl)acetylene was key in the synthesis. Based on a previous developed strategy in our laboratory the best synthetic route towards the title compound was first acetylide coupling of (trimethylsilyl)acetylene to the long-chain protected 10-bromo-1-decanol followed by a second acetylide coupling to the short-chain 1-bromo-4-methylpentane, which resulted in higher yields. Complete spectral data is also presented for the first time for this recently discovered fatty acid and the cis double bond stereochemistry of the natural acid was established. The title compound displayed antiprotozoal activity against Leishmania donovani (IC(50) = 165.5 ± 23.4 μM) and inhibited the leishmania DNA topoisomerase IB enzyme (LdTopIB) with an IC(50) = 62.3 ± 0.7 μM.
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Registered trials
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