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Molecules 2014, 19(1), 279-290;

Synthesis of Novel 2-(Substituted amino)alkylthiopyrimidin-4(3H)-ones as Potential Antimicrobial Agents

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia
Microbial Chemistry Department, Genetic Engineering and Biotechnology Division, National Research Centre, Giza 12622, Egypt
Department of Chemistry, Faculty of Science, Tanta University, Tanta 31527, Egypt
Author to whom correspondence should be addressed.
Received: 29 November 2013 / Revised: 13 December 2013 / Accepted: 16 December 2013 / Published: 27 December 2013
(This article belongs to the Section Organic Chemistry)
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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 3ac 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 5ac and 2-[2-(piperidin-1-yl)ethyl]thiopyrimidin-4(3H)-ones 6a,b, respectively. Treatment of 3ad with N-(2-chloroethyl)morpholine hydrochloride under the same reaction conditions formed the corresponding 2-[2-(morpholin-4-yl)ethyl]thiopyrimidines 6cf. 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 3ad, 4a,b, 5ac, 6af and 7ad 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. View Full-Text
Keywords: 2-thiouracils; pyrimidin-4(3H)-ones; alkylation; antibacterial activity; anti-fungal activity 2-thiouracils; pyrimidin-4(3H)-ones; alkylation; antibacterial activity; anti-fungal activity

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Attia, M.I.; El-Emam, A.A.; Al-Turkistani, A.A.; Kansoh, A.L.; El-Brollosy, N.R. Synthesis of Novel 2-(Substituted amino)alkylthiopyrimidin-4(3H)-ones as Potential Antimicrobial Agents. Molecules 2014, 19, 279-290.

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