title: Synthesis and evaluation as sialidase inhibitors of xylo-configured cyclohexenephosphonates carrying glycerol side-chain mimics.
abstract: Based on a strategy previously reported by us, we have synthesized D-xylo configured cyclohexenephosphonates designed to mimic the transition state of the sialidase reaction. The double bond orientation corresponds to the benchmark inhibitor Neu5Ac2en and we could selectively introduce hydroxyalkyl substituents in order to simulate the glycerol side-chain of neuraminic acid. The inhibitory activity of a set of compounds towards bacterial sialidases was tested and interesting differences in activity were found.
authors.affiliation: Department of Chemistry, University of Konstanz, D-78457, Konstanz, Germany. hansjoerg.streicher@uni-konstanz.de
authors.forename: Hansjörg
authors.initials: H
authors.lastname: Streicher
mesh_terms: D003016:Clostridium perfringens / Q000187:drug effects / Q000201:enzymology / Q000254:growth & development; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000494:pharmacology; D053138:Cyclohexenes; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D005990:Glycerol / Q000138:chemical synthesis* / Q000494:pharmacology; D009439:Neuraminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D012486:Salmonella typhimurium / Q000187:drug effects / Q000201:enzymology / Q000254:growth & development; D014734:Vibrio cholerae / Q000187:drug effects / Q000201:enzymology / Q000254:growth & development
chemical_list: D003510:Cyclohexanes; D053138:Cyclohexenes; D004791:Enzyme Inhibitors; C052568:cyclohexene; D009439:Neuraminidase; D005990:Glycerol