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
8a–
g. 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.
[Display omitted] New compounds with the above structures were synthesized and tested for antimicrobial and anti-inflammatory activity.