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Synthesis and tuberculostatic activity of podands with a dihydropyrimidine fragment

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Abstract

A method for the preparation of 3-oxobutanoate-containing podands differing in the length of the polyether fragment by acetoacetylation of oligo(ethylene glycols) with 2,2,6-trimethyl-4H-1,3-dioxin-4-one upon heating in toluene was optimized. A multi-component Biginelli reaction was used for the formation of the dihydropyrimidine ring on the ether matrix obtained. Tuberculostatic activity of dihydropyrimidine podands in the in vitro experiments against a laboratory strain H37Rv was studied. A combination of dihydropyrimidine and podand fragments imparts tuberculostatic activity to the compounds obtained, which noticeably enhances with the increase in the oxyethylene spacer length.

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Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    E. S. Filatova, O. V. Fedorova, Yu. A. Titova, G. L. Rusinov & V. N. Charushin

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoi, 620219, Ekaterinburg, Russian Federation

    E. S. Filatova, O. V. Fedorova, Yu. A. Titova, P. A. Slepukhin, G. L. Rusinov & V. N. Charushin

  3. Ural Research Institute of Phthisiopulmonology, Russian Ministry of Healthcare, 50 ul. XXII parts´ezda, 620039, Ekaterinburg, Russian Federation

    M. A. Kravchenko & S. N. Skornyakov

Authors
  1. E. S. Filatova
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  2. O. V. Fedorova
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  3. Yu. A. Titova
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  4. P. A. Slepukhin
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  5. M. A. Kravchenko
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  6. S. N. Skornyakov
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  7. G. L. Rusinov
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  8. V. N. Charushin
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Corresponding author

Correspondence to E. S. Filatova.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. G. Sinyashin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1360–1364, May, 2016.

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Filatova, E.S., Fedorova, O.V., Titova, Y.A. et al. Synthesis and tuberculostatic activity of podands with a dihydropyrimidine fragment. Russ Chem Bull 65, 1360–1364 (2016). https://doi.org/10.1007/s11172-016-1462-4

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  • DOI: https://doi.org/10.1007/s11172-016-1462-4

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