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Molecules 2012, 17(3), 3475-3483; doi:10.3390/molecules17033475
Article

Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines

* , ,  and
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 13 January 2012 / Revised: 16 February 2012 / Accepted: 6 March 2012 / Published: 16 March 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract

The reaction of adamantane-1-carbohydrazide (1) with heterocyclic aldehydes, namely 5-(4-chlorophenyl)isoxazole-3-carboxaldehyde (2a), 5-(4-methylphenyl)isoxazole-3-carboxaldehyde (2b), 5-(4-methoxyphenyl)isoxazole-3-carboxaldehyde (2c), 1H-imidazole-2-carboxaldehyde and 2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde, in ethanol, yielded the corresponding N′-heteroarylidene-1-adamantylcarbohydrazides 3a, 3b, 3c, 4 and 5, respectively, in good yields. The 4-acetyl-1,3,4-oxadiazoline analogues 6a‑c were prepared in 48–55% yields by heating their corresponding N′-heteroarylidene-1-adamantylcarbohydrazides 3a–c with acetic anhydride for two hours. Compounds 3a–c, 4, 5 and 6a–c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 4 and 5 displayed potent broad-spectrum antimicrobial activity, while compounds 3a–c showed good activity against the Gram-positive bacteria.
Keywords: adamantane derivatives; 1,3,4-oxadiazoles; isoxazoles; antimicrobial activity adamantane derivatives; 1,3,4-oxadiazoles; isoxazoles; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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El-Emam, A.A.; Alrashood, K.A.; Al-Omar, M.A.; Al-Tamimi, A.-M. Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines. Molecules 2012, 17, 3475-3483.

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