Abstract
New 1-adamanyl-1,3,4-thiadiazole derivatives namely, 5-(1-adamantyl)-1,3,4-thiadiazoline-2-thione
3, 5-(1-adamantyl)-3-(benzyl- or 4-substituted benzyl)-1,3,4-thiadiazoline-2-thione
4a–d, 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-thiadiazoline-2-thiones
5a–c, 2-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]acetic acid
7, (±)-2-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]propionic acid
9, 3-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]propionic acid
11,
N-[5-(1-adamantyl)-1,3,4-thiadiazol-2-yl]-
N′-arylthioureas
15a–c and 5-(1-adamantyl)-1,3,4-thiadiazoline-2-one
16, were synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus
Candida albicans. Compounds
7,
9,
15b and
15c displayed marked activity against the tested Gram-positive bacteria, while compound
3 was highly active against the tested Gram-negative bacteria. Compounds
4b,
7 and
15c were weakly or moderately active against
C. albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenan-induced paw oedema method in rats. The propionic acid derivative
9 produced good dose-dependent anti-inflammatory activity.
New series of 5-(1-adamantyl)-1,3,4-thiadiazoles were synthesized as potential antimicrobial and anti-inflammatory agents. Compounds
3,
7 and
9 displayed marked antibacterial activity. Meanwhile, compound
9 exhibited good dose-dependent anti-inflammatory activity in rats.
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