TY - JOUR AU - Vlasov, S. V. AU - Kovalenko, S. M. AU - Chernykh, V. P. AU - Krolenko, K. Yu. PY - 2015/06/10 Y2 - 2024/03/29 TI - Synthesis and alkylation of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones JF - Journal of Organic and Pharmaceutical Chemistry JA - J. Org. Pharm. Chem. VL - 13 IS - 2(50) SE - Original Researches DO - 10.24959/ophcj.15.822 UR - https://ophcj.nuph.edu.ua/article/view/ophcj.15.822 SP - 30-34 AB - <p>The one-step method for preparation of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones by interaction of 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid with ortho-pnenylediamines using 1,1’-carbonyldiimidazole as a coupling-reagent has been developed. The procedure proposed allows to obtain easily the target products using common reagents and solvents; and it also requires the simple isolation methods. The selectivity of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one interaction with benzyl chlorides in DMF – K2CO3 conditions has been studied using the NOESY spectroscopic method and alternative synthetic approaches; it has been determined that the reaction occurs at position 3 of the thieno[2,3-d] pyrimidine system. The study of the antimicrobial activity by the agar diffusion method for the compounds obtained has shown that 6-(1H-benzimidazol-2-yl)-3-benzyl-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones reveal the antimicrobial activity against the strains of Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa; while the compound with unsubstituted position 3 appeared to be inactive against these strains of microorganisms. However, this compound exhibited the higher inhibitory activity against the Candida albicans fungi.</p> ER -