%0 Journal Article
%T Synthesis of Novel 2-(Substituted amino)alkylthiopyrimidin-4(3H)-ones as Potential Antimicrobial Agents
%A Mohamed I. Attia
%A Ali A. El-Emam
%A Abdulghafoor A. Al-Turkistani
%A Amany L. Kansoh
%A Nasser R. El-Brollosy
%J Molecules
%D 2014
%I MDPI AG
%R 10.3390/molecules19010279
%X 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(3 H)-ones 4a, b. Reaction of 3a每 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(3 H)-ones 5a每 c and 2-[2-(piperidin-1-yl)ethyl]thiopyrimidin-4(3 H)-ones 6a, b, respectively. Treatment of 3a每 d with N-(2-chloroethyl)morpholine hydrochloride under the same reaction conditions formed the corresponding 2-[2-(morpholin-4-yl)ethyl]thiopyrimidines 6c每 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每 d, 4a, b, 5a每 c, 6a每 f and 7a每 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.
%K 2-thiouracils
%K pyrimidin-4(3H)-ones
%K alkylation
%K antibacterial activity
%K anti-fungal activity
%U http://www.mdpi.com/1420-3049/19/1/279