5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and New Cyclic <em>C</em>-Glycoside Analogues from Carbohydrate Precursors with MAO-B, Antimicrobial and Antifungal Activities

5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and New Cyclic <em>C</em>-Glycoside Analogues from Carbohydrate Precursors with MAO-B, Antimicrobial and Antifungal Activities

El-Dayem, Nagwa Said Abd;Yacout, Galila Ahmed;Hassan, Seham Yassen;El-Sadek, Mohamed Mohamed;
molecules 2012 Vol. 17 pp. 7010-7027
281
eldayem201255aryl134oxadiazole2carbonylfuran3carboxylatemolecules

Abstract

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

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