Abstract
The reaction of 5-(1-adamantyl)-4-amino-3-mercapto-1,2,4-triazole (
5
) with various aromatic aldehydes in ethanol or acetic acid yielded the corresponding 4-arylideneamino derivatives
6a–v
. Treatment of the 4-(2,6-difluoro- and dichlorobenzylideneamino) derivatives
6o
and
6q
with 1-substituted piperazines, and formaldehyde solution in ethanol afforded good yields of the corresponding 5-(1-adamantyl)-4-(2,6-dihalobenzylideneamino-2-(4-substituted-1-piperazinylmethyl)-1,2,4-triazoline-3-thiones
7a–p
. 5-(1-Adamantyl)-4-arylideneamino-2-(4-ethoxycarbonyl-1-piperidylmethyl)-1,2,4-triazoline-3-thiones
8a–n
, were similarly prepared
via
the reaction of the corresponding arylideneamino derivative with ethyl 4-piperidinecarboxylate and formaldehyde solution in ethanol. Compounds
6a–v
,
7a–p
and
8a–n
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 showed good or moderate activities, particularly against the tested Gram-positive bacteria. In addition, the
in vivo
anti-inflammatory activity of 21 compounds was determined using the carrageenan-induced paw oedema method in rats. Compounds
7d
,
7g
,
7i, 7j
,
7l
,
8c
,
8e
and
8l
showed good or moderate dose-dependent activity in this area.