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,* email
Received: 29 November 2013; in revised form: 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
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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MDPI and ACS Style

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.

AMA Style

Attia MI, El-Emam AA, Al-Turkistani AA, Kansoh AL, El-Brollosy NR. Synthesis of Novel 2-(Substituted amino)alkylthiopyrimidin-4(3H)-ones as Potential Antimicrobial Agents. Molecules. 2014; 19(1):279-290.

Chicago/Turabian Style

Attia, Mohamed I.; El-Emam, Ali A.; Al-Turkistani, Abdulghafoor A.; Kansoh, Amany L.; El-Brollosy, Nasser R. 2014. "Synthesis of Novel 2-(Substituted amino)alkylthiopyrimidin-4(3H)-ones as Potential Antimicrobial Agents." Molecules 19, no. 1: 279-290.


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