Building a successful structural motif into sialylmimetics-cyclohexenephosphonate monoesters as pseudo-sialosides with promising inhibitory properties.
A variable synthesis of a new class of sialylmimetics which provides access to pseudo-sialosides containing the successful cyclohexene motif in the sialic acid mimicking part has been developed. The D- and L-xylo cyclohexenephosphonate scaffolds allow attachment of selected aglycons or aglycon mimetics via mixed phosphonate diester strategies and some target compounds thus synthesized displayed promising inhibitory properties when tested with parasitic or bacterial sialidases.
Streicher
Hansjörg
H
Chemistry Department, University of Sussex, Brighton, UK. H.Streicher@sussex.ac.uk
Busse
Heike
H
D000818:Animals; D001554:Benzene / Q000737:chemistry; D003016:Clostridium perfringens / Q000187:drug effects / Q000201:enzymology; D003510:Cyclohexanes / Q000737:chemistry*; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008745:Methylation; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D009439:Neuraminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010756:Phosphoric Acids / Q000737:chemistry*; D012486:Salmonella typhimurium / Q000187:drug effects / Q000201:enzymology; D013329:Structure-Activity Relationship; D014349:Trypanosoma cruzi / Q000187:drug effects / Q000201:enzymology
D003510:Cyclohexanes; D004791:Enzyme Inhibitors; D004952:Esters; D010756:Phosphoric Acids; C030242:phosphoric acid; D009439:Neuraminidase; D019158:N-Acetylneuraminic Acid; D001554:Benzene