Journal
MOLECULES
Volume 16, Issue 6, Pages 4764-4774Publisher
MDPI AG
DOI: 10.3390/molecules16064764
Keywords
synthesis; 5-alkyluracils; 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-dione; antimicrobial activity
Funding
- Research Center of the College of Pharmacy, King Saud University
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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.
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