S. Vlasov, V. Chernykh, T. Osolodchenko
Sep 11, 2015
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Abstract
The effective method for the synthesis of ethyl 3-alkyl-5-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydro-thieno[2,3-d]pyrimidine-6-carboxylate derivatives by interaction of diethyl 3-methyl-5-{[(methylsulfanyl) carbothioyl]amino}thiophene-2,4-dicarboxylate with low aliphatic amines in the 2-propanol medium has been developed. The conditions proposed facilitate isolation and perceptibly improve the yields of the target thiones. The further modification of ethyl 3-alkyl-5-methyl-4-oxo-2-thioxo-1,2,3,4-tetra-hydrothieno[2,3-d]pyrimidine-6-carboxylate has been performed by alkylation with chloroacetamides and 3-aryl-5-(chloromethyl)-1,2,4-oxadiazoles (DMF-triethylamine). The structure of the compounds obtained has been confirmed using the NMR spectroscopic methods; the products of alkylation have the signals of the carbethoxy group as two signals in the ranges of 1.27-1.30 ppm (3Н, t) and 4.24-4.29 (2Н, q), and the signal of SCH 2 protons in the range of 4.22-4.93 ppm. The study of the antimicrobial activity for the functionalized derivatives of thieno[2,3-d]pyrimidine, the corresponding ethyl 3-alkyl-5-methyl-2-({2-[arylamino]-2-oxoethyl}thio)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carb-oxylates and ethyl 3-alkyl-5-methyl-4-oxo-2-{[(3-aryl-1,2,4-oxadiazol-5-yl)methyl]thio}-3,4-dihydro-thieno[2,3-d]pyrimidine-6-carboxylate has shown their moderate antimicrobial properties, while for some compounds with the n-butyl substituent at position 3 possess the high inhibitory activity against Candida albicans fungi growth.