Синтез та алкілювання 6-(1H-бензімідазол-2-іл)-5-метилтієно[2,3-d]піримідин-4(3H)-онів

• Date: 2015
• Main Authors: Vlasov, S. V., Kovalenko, S. M., Chernykh, V. P., Krolenko, K. Yu.
• Format: Article
• Language: English
• Published: National University of Pharmacy 2015
• Subjects: тіофен; піримідин; імідазол; алкілювання; УДК 547.732; 547.853; 547.781; 66.095.253
• Online Access: https://ophcj.nuph.edu.ua/article/view/ophcj.15.822
• Journal Title: Journal of Organic and Pharmaceutical Chemistry

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.