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Synthesis and antimicrobial evaluation of farnesyl diphosphate mimetics
Ian J S Fairlamb1, Julia M Dickinson, Rachael O'Connor
1Department of Chemistry and Materials, John Dalton Building, The Manchester Metropolitan University, Chester Street, Manchester M20 5GD, UK. ijsf1@york.ac.uk
Abstract:
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.