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Synthesis and antimicrobial evaluation of farnesyl diphosphate mimetics

✍ Scribed by Ian J.S. Fairlamb; Julia M. Dickinson; Rachael O’Connor; Louis H. Cohen; Christa F. van Thiel

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
324 KB
Volume
31
Category
Article
ISSN
0045-2068

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✦ Synopsis

The synthesis and first antimicrobial evaluation of farnesyl diphosphate mimetics are described. Several analogues (10, 12, 13, and 20) are inhibitors of Candida albicans, Shizosaccharomyces pombe, and Saccharomyces cerevisiae. The activities of analogues 10, 12, and 13, which contain a omega-phenyl moiety and a diphosphate isostere, are not attributable to inhibition of sterol biosynthesis via squalene synthase. Two geranyl phenylsulphones (14 and 15) are potent inhibitors of Escherichia coli. Analogue 15 exhibits potent activity towards Salmonella typhimurium and Pseudomonas aeruginosa (MIC-2 microg/mL) and represents the first type of semi-synthetic terpenoid allylic sulphone active against these bacteria.

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