Email this article 6-Trifluoromethyl-2-thiouracil and its analogs in reactions with 4-bromobutyl acetate and 2-bromoacetophenone
- Authors: Ezhikova M.A.1, Kodess M.I.1,2, Ulitko M.V.2, Saloutin V.I.1,2, Ivanova A.E.1, Khudina O.G.1, Burgart Y.V.1,2, Pervova M.G.1
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Affiliations:
- I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
- Ural Federal University named after the first President of Russia B. N. Yeltsin
- Issue: Vol 68, No 6 (2019)
- Pages: 1190-1195
- Section: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/243399
- DOI: https://doi.org/10.1007/s11172-019-2538-8
- ID: 243399
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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.
About the authors
M. A. Ezhikova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: saloutin@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Yekaterinburg, 620990
M. I. Kodess
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal University named after the first President of Russia B. N. Yeltsin
Email: saloutin@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Yekaterinburg, 620990; 19 ul. Mira, Yekaterinburg, 620002
M. V. Ulitko
Ural Federal University named after the first President of Russia B. N. Yeltsin
Email: saloutin@ios.uran.ru
Russian Federation, 19 ul. Mira, Yekaterinburg, 620002
V. I. Saloutin
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal University named after the first President of Russia B. N. Yeltsin
Author for correspondence.
Email: saloutin@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Yekaterinburg, 620990; 19 ul. Mira, Yekaterinburg, 620002
A. E. Ivanova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: saloutin@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Yekaterinburg, 620990
O. G. Khudina
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: saloutin@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Yekaterinburg, 620990
Ya. V. Burgart
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal University named after the first President of Russia B. N. Yeltsin
Email: saloutin@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Yekaterinburg, 620990; 19 ul. Mira, Yekaterinburg, 620002
M. G. Pervova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: saloutin@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Yekaterinburg, 620990
