Design, synthesis and biological evaluation of hetaryl-nucleoside derivatives as inhibitors of chitin synthase.
We report here the design, synthesis and biological evaluation of new models of sugar analogues for chitin synthase. These UDP-GlcNAc mimetics associate a sugar-mimicking hetaryl group and uridine, linked with different pyrophosphate bioisosteres. The compounds displayed weak inhibition activity on chitin synthase and their antifungal potencies have been assayed against a large variety of pathogenic fungi.
Laboratoire Réactions Sélectives et Applications UMR 6519, UFR Sciences, CNRS BP 1039, 51687 Reims Cedex 2, France.
Jean-Bernard
JB
Behr
Thierry
T
Gourlain
Abdellatif
A
Helimi
Georges
G
Guillerm
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002687:Chitin Synthase / Q000037:antagonists & inhibitors*; D015195:Drug Design; D005658:Fungi / Q000187:drug effects; D005944:Glucosamine / Q000031:analogs & derivatives*; D020128:Inhibitory Concentration 50; D018716:Molecular Mimicry; D009705:Nucleosides / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D009705:Nucleosides; C026712:UDP-glucosamine; D002687:Chitin Synthase; D005944:Glucosamine