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.
Highlights
C-glycosides have received a great deal of attention from the synthesis and medicinal chemistry community, due to their increased stability to hydrolysis as well as their presence in a number of interesting natural products [1]
Several 1,3,4-oxadiazole derivatives were identified as potentially active antimycobacterial [7,8], antitubercular [9], anticonvulsant [10] and anticancer [11] agents, and reported as enzyme tyrosinase inhibitors [12]
In light of these interesting biological activities, it became interested in synthesizing some new C-glycosides of substituted 1,3,4-oxadiazole derivatives and evaluating their antimicrobial potential
Summary
C-glycosides have received a great deal of attention from the synthesis and medicinal chemistry community, due to their increased stability to hydrolysis as well as their presence in a number of interesting natural products [1]. Anti-inflammatory [3,4], antimicrobial [4], anti-hepatitis B [5] and anti-diarrheal activity [6] of some new 1,3,4-oxadiazole derivatives was reported. Several 1,3,4-oxadiazole derivatives were identified as potentially active antimycobacterial [7,8], antitubercular [9], anticonvulsant [10] and anticancer [11] agents, and reported as enzyme tyrosinase inhibitors [12]. In light of these interesting biological activities, it became interested in synthesizing some new C-glycosides of substituted 1,3,4-oxadiazole derivatives and evaluating their antimicrobial potential
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