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Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: IX. N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl) Ureas and Thioureas

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Abstract

N,N′-Disubstituted ureas and thioureas containing a lipophilic optically active natural bicyclic moiety have been synthesized by reactions of (R)-, (S)-, and (RS)-1,1,7-trimethylbicyclo[2.2.1]heptan-2-amines with aromatic isocyanates and isothiocyanates in up to 85% and 88% yield, respectively, with the goal of estimating enantiomeric stereospecificity of human soluble epoxide hydrolase (hsEH). The synthesized com­pounds are promising as inhibitors of RNA viruses and hsEH.

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Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 19-33-60024).

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Authors and Affiliations

  1. Volgograd State Technical University, 400005, Volgograd, Russia

    Ya. P. Kuznetsov, E. K. Degtyarenko, V. V. Burmistrov, M. H. Abbas Saeef & A. A. Vernigora

  2. Volzhsky Polytechnic Institute (Branch), Volgograd State Technical University, 404121, Volzhsky, Russia

    D. A. Pitushkin & G. M. Butov

Authors
  1. Ya. P. Kuznetsov
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  2. E. K. Degtyarenko
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  3. V. V. Burmistrov
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  4. M. H. Abbas Saeef
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  5. D. A. Pitushkin
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  6. A. A. Vernigora
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  7. G. M. Butov
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Corresponding author

Correspondence to G. M. Butov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 4, pp. 485–496 https://doi.org/10.31857/S0514749221040030.

For communication VIII, see [1].

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Kuznetsov, Y.P., Degtyarenko, E.K., Burmistrov, V.V. et al. Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: IX. N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl) Ureas and Thioureas. Russ J Org Chem 57, 515–523 (2021). https://doi.org/10.1134/S1070428021040035

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