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Molecules 2012, 17(6), 7010-7027; doi:10.3390/molecules17067010

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

1
Chemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt
2
Biochemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt
*
Author to whom correspondence should be addressed.
Received: 1 April 2012 / Revised: 27 April 2012 / Accepted: 9 May 2012 / Published: 7 June 2012
(This article belongs to the Special Issue Heterocycles)
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Abstract

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.
Keywords: carbohydrazone; isopropylidene; triazole; oxadiazole; monoamine oxidase-B carbohydrazone; isopropylidene; triazole; oxadiazole; monoamine oxidase-B
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

El-Sadek, M.M.; Hassan, S.Y.; El-Dayem, N.S.A.; Yacout, G.A. 5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and New Cyclic C-Glycoside Analogues from Carbohydrate Precursors with MAO-B, Antimicrobial and Antifungal Activities. Molecules 2012, 17, 7010-7027.

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