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Molecules 2014, 19(1), 279-290; doi:10.3390/molecules19010279
Article

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

1, 1, 1, 2 and 1,3,*
1 Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia 2 Microbial Chemistry Department, Genetic Engineering and Biotechnology Division, National Research Centre, Giza 12622, Egypt 3 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 Synthesis)
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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 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.
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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