Abstract
The alkylation of 6-(polyfluoro)alkyl-2-thiouracils with 4-bromobutyl acetate in refluxing acetonitrile in the presence of K2CO3 proceeds regioselectively to give S, O-disubstituted pyrimidines as the major products and S,N-isomers as the minor ones, whereas the use of 2-bromoacetophenone as an alkylating agent results in the formation of the S,O-isomer. 6-Trifluoromethyl-2-thiouracil and 2-(2-oxo-2-phenylethylthio)-4-(2-oxo-2-phenylethoxy)-6-trifluoromethyl-pyrimidine exhibited marked tuberculostatic activity. 6-Trifluoromethyl-2-thiouracil did not exert a significant cytotoxic effect on the HeLa cell culture and human dermal fibroblasts.
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Dedicated to Academician of the Russian Academy of Sciences O. N. Chupakhin on the occasion of his 85th birthday.
Published in Russian in Izyestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1190–1195, June, 2019.
We are grateful to M. A. Kravchenko (Ural Research Institute for Phthisiopulmonology, Ministry of Health of the Russian Federation) for evaluating antituberculosis activity of the synthesized compounds.
This work was financially supported by the Ural Branch of the Russian Academy of Sciences (Program No. 18-3-3-12) and performed using facilities of the Joint Use Center “Spectroscopy and Analysis of Organic Compounds” (JUC SAOC).
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Ivanova, A.E., Khudina, O.G., Burgart, Y.V. et al. 6-Trifluoromethyl-2-thiouracil and its analogs in reactions with 4-bromobutyl acetate and 2-bromoacetophenone. Russ Chem Bull 68, 1190–1195 (2019). https://doi.org/10.1007/s11172-019-2538-8
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DOI: https://doi.org/10.1007/s11172-019-2538-8