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.
Highlights
Nonsteroidal anti-inflammatory drugs (NSAIDs) are among the most widely used therapeutics, primarily for the treatment of pain and inflammation in arthritis
In continuation to our interest in the chemical and pharmacological properties of adamantane derivatives [6,11,14,15,16], we report the synthesis, antimicrobial and anti-inflammatory activities of a new series of 5-(1-adamantyl)-4arylideneamino-3-mercapto-1,2,4-triazoles and their piperazinomethyl and piperidinomethyl
5-(1-Adamantyl)-4-amino-3-mercapto-1,2,4-triazole (5) was prepared starting from adamantane-1carboxylic acid (1) via esterification with methanol to yield the methyl ester 2, which was subsequently reacted with hydrazine to yield adamantane-1-carboxylic acid hydrazide (3)
Summary
Nonsteroidal anti-inflammatory drugs (NSAIDs) are among the most widely used therapeutics, primarily for the treatment of pain and inflammation in arthritis. 1,2,4-Triazole derivatives were reported to possess diverse biological activities, such as antibacterial [19,20,21] and anti-inflammatory [22,23,24,25] properties. 5-substituted-4-arylideneamino-3-mercapto-1,2,4-triazoles and their piperazinomethyl derivatives were reported to exhibit significant antimicrobial activity [26,27,28]. In continuation to our interest in the chemical and pharmacological properties of adamantane derivatives [6,11,14,15,16], we report the synthesis, antimicrobial and anti-inflammatory activities of a new series of 5-(1-adamantyl)-4arylideneamino-3-mercapto-1,2,4-triazoles and their piperazinomethyl and piperidinomethyl Mannich bases
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