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Molecules 2011, 16(6), 4764-4774; doi:10.3390/molecules16064764

Synthesis and Antimicrobial Activity of Some Novel 5-Alkyl-6-Substituted Uracils and Related Derivatives

, ,  and *
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 13 May 2011 / Revised: 31 May 2011 / Accepted: 1 June 2011 / Published: 8 June 2011
(This article belongs to the Section Medicinal Chemistry)
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6-Chloro-5-ethyl-, n-propyl- and isopropyluracils 5a-c were efficiently prepared from the corresponding 5-alkybarbituric acids 3a-c via treatment with phosphorus oxychloride and N,N-dimethylaniline to yield the corresponding 5-alkyl-2,4,6-trichloro-pyrimidines 4a-c, which were selectively hydrolyzed by heating in 10% aqueous sodium hydroxide for 30 minutes. The reaction of compounds 5a-c with 1-substituted piperazines yielded the corresponding 5-alkyl-6-(4-substituted-1-piperazinyl)uracils 6a-j. The target 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-diones 7a-c were prepared via the reaction of 5a-c with sodium azide. Compounds 6a-j and 7a-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. Compound 6h displayed potent broad-spectrum antibacterial activity, while compound 6b showed moderate activity against the Gram-positive bacteria. All the tested compounds were practically inactive against Candida albicans.
Keywords: synthesis; 5-alkyluracils; 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-dione; antimicrobial activity synthesis; 5-alkyluracils; 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-dione; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Al-Turkistani, A.A.; Al-Deeb, O.A.; El-Brollosy, N.R.; El-Emam, A.A. Synthesis and Antimicrobial Activity of Some Novel 5-Alkyl-6-Substituted Uracils and Related Derivatives. Molecules 2011, 16, 4764-4774.

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