Synthesis and biological activity of desmethoxy analogues of coruscanone A
Language English Country Great Britain, England Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
21903391
DOI
10.1016/j.bmcl.2011.08.059
PII: S0960-894X(11)01154-1
Knihovny.cz E-resources
- MeSH
- Antifungal Agents chemical synthesis chemistry pharmacology MeSH
- Cell Line MeSH
- Candida drug effects MeSH
- Cyclopentanes chemical synthesis chemistry pharmacology MeSH
- 4-Butyrolactone analogs & derivatives chemical synthesis chemistry pharmacology MeSH
- Candidiasis drug therapy MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Mice MeSH
- Cell Line, Tumor MeSH
- Structure-Activity Relationship MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Antifungal Agents MeSH
- butenolide MeSH Browser
- coruscanone A MeSH Browser
- Cyclopentanes MeSH
- 4-Butyrolactone MeSH
A series of simple desmethoxy analogues of coruscanone A was prepared via a novel version of Ti(iPrO)(4)-mediated Knoevenagel condensation of cyclopentenedione with substituted benzaldehydes and cinnamic aldehydes, and the compounds were evaluated for antifungal activity and cytotoxicity. The most potent 2-benzylidenecyclopent-4-ene-1,3-dione possessed antifungal effect comparable to coruscanone A and a somewhat broader spectrum of activity against Candida species. The compound was also superior to fluconazole against several non-albicans Candida sp. Evaluation of the ability of the compound to influence cell proliferation using two different assays showed that 2-benzylidenecyclopent-4-ene-1,3-dione has lower cytotoxicity compared to the natural product.
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