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.
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 bisaroylhydrazones 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.
Chemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt. elsadek_mm@yahoo.com
Mohamed Mohamed
MM
El-Sadek
Seham Yassen
SY
Hassan
Nagwa Said Abd
NS
El-Dayem
Galila Ahmed
GA
Yacout
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D004789:Enzyme Activation / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006027:Glycosides; D008995:Monoamine Oxidase / Q000378:metabolism*; D009005:Monosaccharides / Q000737:chemistry* / Q000494:pharmacology*; D010069:Oxadiazoles / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; C438934:C-glycoside; D006027:Glycosides; D009005:Monosaccharides; D010069:Oxadiazoles; D008995:Monoamine Oxidase