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Please use this identifier to cite or link to this item: http://hdl.handle.net/123456789/17056

Title: Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles
Authors: Adnan A. Kadi a
Nasser R. El-Brollosy
Omar A. Al-Deeb a
Keywords: 1-Adamantyl derivatives; 1,3,4-Oxadiazoles; 1,3,4-Thiadiazoles; Anti-inflammatory activity; Antimicrobial activity
Issue Date: 2007
Publisher: Elsevier
Abstract: Reaction of 1-adamantanecarbonyl chloride with certain carboxylic acid hydrazides in pyridine yielded the corresponding N-acyl adamantane- 1-carbohydrazide derivatives 3aej, which were cyclized to the corresponding 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles 4aej via heating with phosphorus oxychloride. Treatment of 1-adamantylisothiocyanate with some carboxylic acid hydrazides in ethanol yielded the corresponding 1-acyl-4-(1-adamantyl)-3-thiosemicarbazides 7aeg, which were cyclized to the corresponding 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazole derivatives 8aeg. Compounds 4aej, 7aeg, and 8aeg were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several derivatives produced good or moderate activities particularly against the tested Gram-positive bacteria Bacillus subtilis. Meanwhile, compounds 4i and 8g displayed marked antifungal activity against C. albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenin-induced paw oedema method in rats. The oxadiazole derivatives 4c, 4g, 4i and 4j produced good dose-dependent anti-inflammatory activity.
URI: http://hdl.handle.net/123456789/17056
Appears in Collections:College of Pharmacy

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