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Molecules 2010, 15(4), 2526-2550; doi:10.3390/molecules15042526
Article

Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives

1, 1, 1, 2, 3 and 1,*
1 Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia 2 Department of Microbiology, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt 3 Department of Pharmacology and Toxicology, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
* Author to whom correspondence should be addressed.
Received: 8 March 2010 / Revised: 29 March 2010 / Accepted: 2 April 2010 / Published: 9 April 2010
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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.
Keywords: 1-adamantyl derivatives; 1,2,4-triazoles; antimicrobial activity; anti-inflammatory activity 1-adamantyl derivatives; 1,2,4-triazoles; antimicrobial activity; anti-inflammatory activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Al-Omar, M.A.; Al-Abdullah, E.S.; Shehata, I.A.; Habib, E.E.; Ibrahim, T.M.; El-Emam, A.A. Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives. Molecules 2010, 15, 2526-2550.

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