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Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XII. N-(1,3,3-Trimethylbicyclo[2.2.1]heptan-2-yl)-N′-R-ureas and -thioureas

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Abstract

N,N′-Disubstituted ureas and thioureas containing a lipophilic optically active bicyclic fragment of natural origin were synthesized by reaction of (R)- and (S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-amine (prepared from the natural terpenoid fenchone) with aromatic isocyanates and isothiocyanates in up to 88 and 87% yield, respectively, with the goal of assessing the enantiomeric specificity of human soluble epoxide hydrolase (hsEH). The synthesized compounds were found to be promising as inhibitors of RNA virus replication and hsEH.

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ACKNOWLEDGMENTS

The study was performed using the equipment of the joint center at the MIREA Russian Technological University under support by the Ministry of Science and Higher Education of the Russian Federation.

Funding

This study was financially supported 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, A. A. Vernigora, E. K. Degtyarenko, M. H. Abbas Saeef & V. V. Burmistrov

  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. A. A. Vernigora
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  3. E. K. Degtyarenko
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  4. M. H. Abbas Saeef
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  5. D. A. Pitushkin
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  6. V. V. Burmistrov
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  7. G. M. Butov
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Corresponding author

Correspondence to G. M. Butov.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 12, pp. 1657–1668 https://doi.org/10.31857/S0514749221120016.

For communication XI, see [1].

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Kuznetsov, Y.P., Vernigora, A.A., Degtyarenko, E.K. et al. Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XII. N-(1,3,3-Trimethylbicyclo[2.2.1]heptan-2-yl)-N′-R-ureas and -thioureas. Russ J Org Chem 57, 1891–1900 (2021). https://doi.org/10.1134/S1070428021120010

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