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• Al-Turkistani, A
• Al-Deeb, O
• El-Brollosy, N
• El-Emam, A
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• Al-Turkistani, A
• Al-Deeb, O
• El-Brollosy, N
• El-Emam, A
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• Al-Turkistani, A
• Al-Deeb, O
• El-Brollosy, N
• El-Emam, A

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

Article

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

Abdulghafoor A. Al-Turkistani, Omar A. Al-Deeb, Nasser R. El-Brollosy and Ali A. El-Emam*

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; in revised form: 31 May 2011 / Accepted: 1 June 2011 / Published: 8 June 2011

(This article belongs to the Section Medicinal Chemistry)

Download PDF Full-Text [143 KB, uploaded 8 June 2011 11:42 CEST]

Abstract: 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

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