5-(5-Aryl-134-oxadiazole-2-carbonyl)furan-3-carboxylate and New Cyclic C-Glycoside Analogues from Carbohydrate Precursors with MAO-B Antimicrobial and Antifungal Activities

摘要

Cyclization of acyclic C-glycoside derivatives >1a,b to >2a,b as the major isomers, and >4a,b as the minor isomers were carried out. The isopropylidene derivatives >3a,b were prepared, as well as the hydrazide derivative >6, which was condensed with a variety of aldehydes to give hydrazones >7a–e which were also prepared from the compounds >12a–e. Acetylation of >7a,d gave the corresponding acetyl derivatives >8a,d, respectively. In addition, the dicarbonyl compound >9 was prepared in the hydrate form, which reacted with a number of aroylhydrazines to give the corresponding bisaroyl-hydrazones >10a–d, which were cyclized into 1,3,4-oxadiazoles >11a–d. Furthermore, two of the prepared compounds were examined to show the ability to activate MAO-B. In addition a number of prepared compounds showed antibacterial and antiviral activities.