Pyrimidine-5-carbonitriles II: Synthesis and Antimicrobial Activity of Novel 6-Alkyl-2,4-disubstituted pyrimidine-5-carbonitriles

Abstract

New series of 6-alkyl-2,4-disubstituted pyrimidine-5-carbonitriles namely, 6-alkyl-2-thiouracil-5-carbonitriles 4c,d, 6-alkyl-2-arylmethylsulfanyl-3,4-dihydro-4-oxopyrimidine-5-carbonitriles 5a-p, 6-alkyl-2-(2-methoxyethylsulfanyl)-3,4-dihydro-4-oxopyrimidine-5-carbonitriles 6a-d, 6-alkyl-2-benzyloxymethylsulfanyl-3,4-dihydro-4-oxopyrimidine-5-carbonitriles 7a-c, 6-alkyl-2-(5-nitrofuran-2-ylmethylsulfanyl)-3,4-dihydro-4-oxopyrimidine-5-carbonitriles 8a-d, 6-alkyl-4-arylthio-2-(benzylsulfanyl)pyrimidine-5-carbonitriles 10a, b and 2-benzylsulfanyl-4-[4-(2-methoxyphenyl)-1-piperazinyl]-6-pentylpyrimidine-5-carbonitrile 11, were 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 4d, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5 l, 5p, 7a, 7b, 7c, 8a, 8b, 8c, 8d and 11 -displayed marked antibacterial activity particularly against the tested Gram-positive bacteria. Meanwhile, none of these compounds were proved to be active against Candida albicans.

Crystal structure of 2-[(4-fluorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile, C16H16FN3OS

“…A large number of pyrimidine-based antimetabolites are currently used as potent and selective anticancer activity [10][11][12]. In addition, marked antibacterial and antifungal activities were observed for several pyrimidine-5-carbonitrile derivatives [13][14][15][16][17]. Here, we report the crystal structure of the recently synthesized [16] title compound (C 16 H 16 FN 3 OS).…”

Crystal structure of 6-oxo-4-propyl-2-(propylthio)-1,6-dihydropyrimidine-5-carbonitrile, C11H15N3OS

“…Large array of pyrimidine-based analogues have emerged as useful therapies against human immunode ciency viruses (HIV) [5][6][7][8], hepatitis B viruses (HBV) [9], herpes simplex viruses (HSV) [10,11], in uenza viruses [12] and varicella-zoster virus (VZV) [13]. Moreover, several pyrimidine derivatives were reported to display antibacterial [14][15][16][17] and antifungal [18] activities. Taking into consideration the diverse chemotherapeutic properties of pyrimidine-5-carbonitrile derivatives, we report herein the synthesis and the crystal structure of the title compound.…”

Crystal structure of 6-(phenylsulfanyl)-5-propylpyrimidine-2,4(1H,3H)- dione, C13H14N2O2S

“…In addition, potent anticancer [7][8][9][10] and antimicrobial activities [11,12] was observed for several pyrimidine-2,4-diones. In continuation to our interest in the chemical and pharmacological properties of pyrimidine and uracil derivatives [13][14][15][16] we synthesized the title compound as potential chemotherapeutic agent. X-ray crystallography is a decisive analytical tool which can confirm the configuration of compounds.…”