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Synthesis of novel 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles as potential antimicrobial agents.

European journal of medicinal chemistry (2011-08-19)
Ebtehal S Al-Abdullah, Abdul-Rahman M Al-Obaid, Omar A Al-Deeb, Elsayed E Habib, Ali A El-Emam
ABSTRACT

New series of 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles namely, 2-substitued thio-6-phenyl-3,4-dihydro-4-oxopyrimidine-5-carbonitriles (5a-d, 6, 7a-d, 8), 2-(4-chlorobenzylthio)-4-chloro-6-phenylpyrimidine-5-carbonitrile (9), 2-(4-chlorobenzylthio)-4-arylthio-6-phenylpyrimidine-5-carbonitriles (10a-d) and 2-(4-chlorobenzylthio)-4-arylamino-6-phenylpyrimidine-5-carbonitriles (11a-d) was synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 5b, 5c, 6, 7a, 7b, 7c, 9 and 11a displayed marked antibacterial activity particularly against the tested Gram-positive bacteria, while compounds 6, 7c, 7d and 9 were moderately or weakly active against C. albicans.

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Sigma-Aldrich
Clotrimazole
Sigma-Aldrich
Ampicillin trihydrate, 900-1050 μg/mg anhydrous basis (HPLC)
Sigma-Aldrich
Ampicillin, meets USP testing specifications
Supelco
Ampicillin trihydrate, VETRANAL®, analytical standard