Abstract
5-Alkyl-6-(substituted benzyl)-2-thiouracils 3a,c were reacted with (2-chloroethyl) diethylamine hydrochloride to afford the corresponding 2-(2-diethylamino)ethylthiopyrimidin-4(3H)-ones 4a,b. Reaction of 3a–c with N-(2-chloroethyl)pyrrolidine hydrochloride and/or N-(2-chloroethyl)piperidine hydrochloride gave the corresponding 2-[2-(pyrrolidin-1-yl)ethyl]-thiopyrimidin-4(3H)-ones 5a–c and 2-[2-(piperidin-1-yl)ethyl]thiopyrimidin-4(3H)-ones 6a,b, respectively. Treatment of 3a–d with N-(2-chloroethyl)morpholine hydrochloride under the same reaction conditions formed the corresponding 2-[2-(morpholin-4-yl)ethyl]thiopyrimidines 6c–f. On the other hand, 3a,b were reacted with N-(2-bromoethyl)phthalimide and/or N-(3-bromopropyl)phthalimide to furnish the corresponding 2-[2-(N-phthalimido)ethyl]-pyrimidines 7a,b and 2-[3-(N-phthalimido)-propyl]pyrimidines 7c,d, respectively. Compounds 3a–d, 4a,b, 5a–c, 6a–f and 7a–d were screened against Gram-positive bacteria (Staphylococcus aureus ATCC 29213, Bacillus subtilis NRRL 4219 and Bacillus cereus), yeast-like pathogenic fungus (Candida albicans ATCC 10231) and a fungus (Aspergillusniger NRRL 599). The best antibacterial activity was displayed by compounds 3a, 3b, 4a, 5a, 5b, 6d, 6f, 7b and 7d, whereas compounds 4b, 5b, 5c, 6a, 6b and 6f exhibited the best antifungal activity.
Highlights
In chemotherapy pyrimidines are considered as privileged structures with a large spectrum of biological activities
The chemotherapeutic efficacy of pyrimidines may be due to their ability to inhibit vital enzymes responsible for nucleic acid biosynthesis such as reverse transcriptase, dihydrofolate reductase, uridine and thymidine phosphorylase, as well as thymidylate synthetase
We found it of interest to evaluate the antimicrobial activity for such pyrimidine derivatives
Summary
In chemotherapy pyrimidines are considered as privileged structures with a large spectrum of biological activities. They are known very widely in Nature since they are components of RNA and DNA. Several pyrimidine derivatives have been reported as antithyroid [24] and antimicrobial agents [25,26,27,28,29,30], as well as human thymidine and uridine phosphorylase inhibitors [31,32,33]. As a part of our continuing interest in the chemistry of pyrimidines [30,34,35,36,37,38,39,40,41,42], the synthesis and antimicrobial evaluation of some novel 2-(substituted amino)alkylthiopyrimidin-4(3H)-one derivatives have been investigated
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