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Please use this identifier to cite or link to this item: http://hdl.handle.net/123456789/6482

Title: Synthesis, antimicrobial, and anti-inflammatory 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: Kadi, Adnan A.
El-Brollosy, Nasser R.
Al-Deeb, Omar A.
Habib, Elsayed E.
Ibrahim, Tarek M.
El-Emam, Ali A.
Keywords: Adamantyl derivatives
Oxadiazoles
Thiadiazoles
Anti-inflammatory activity
Antimicrobial activity
Issue Date: 2007
Publisher: Elsevier Masson SAS
Citation: European Journal of Medicinal Chemistry: 42; 235-242
Abstract: Reaction of 1-adamantanecarbonyl chloride with certain carboxylic acid hydrazides in pyridine yielded the corresponding N-acyl adamantane- 1-carbohydrazide derivatives 3a-j, which were cyclized to the corresponding 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles 4a-j 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 7a-g, which were cyclized to the corresponding 2-(1-adamantylamino)-5- substituted-1,3,4-thiadiazole derivatives 8-eg. Compounds 4a-j, 7a-g, and 8a-g 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.
Description: Author: 1, From the Department of Pharmaceutical Chemistry, P. O. Box 2457, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
URI: http://hdl.handle.net/123456789/6482
ISSN: 0223-5234
Appears in Collections:King Saud University Initial Collection

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