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Synthesis and Antimicrobial Activity of Some Novel 5-Alkyl-6-Substituted Uracils and Related Derivatives
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
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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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.
Al-Turkistani AA, Al-Deeb OA, El-Brollosy NR, El-Emam AA. Synthesis and Antimicrobial Activity of Some Novel 5-Alkyl-6-Substituted Uracils and Related Derivatives. Molecules. 2011; 16(6):4764-4774.
Al-Turkistani, Abdulghafoor A.; Al-Deeb, Omar A.; El-Brollosy, Nasser R.; El-Emam, Ali A. 2011. "Synthesis and Antimicrobial Activity of Some Novel 5-Alkyl-6-Substituted Uracils and Related Derivatives." Molecules 16, no. 6: 4764-4774.