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Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XI. 1-[(Adamantan-1 yl)alkyl]-3-arylselenoureas

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Abstract

A series of N,N′-disubstituted selenoureas containing an adamantane fragment have been synthesized in 23–75% yields. Procedures for the isolation and purification of aromatic isoselenocyanates have been improved. The chemical shift of the C=Se carbon nucleus in the 13C NMR spectra of selenoureas has been refined. The synthesized selenoureas have been found to be promising as inhibitors of not only epoxide hydrolase (sEH-H) but also phosphatase domains (sEH-P) of human soluble epoxide hydrolase.

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Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 20-03-00298).

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Authors and Affiliations

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

    Ya. P. Kuznetsov, E. V. Rasskazova, D. A. Pitushkin, V. V. Burmistrov & G. M. Butov

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

    D. A. Pitushkin & G. M. Butov

  3. State Research Institute of Chemistry and Technology of Organoelement Compounds, 105118, Moscow, Russia

    A. V. Eshtukov

  4. Vavilov All-Russian Institute of Plant Genetic Resources, 190000, St. Petersburg, Russia

    V. V. Vasipov

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  1. Ya. P. Kuznetsov
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Correspondence to G. M. Butov.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 929–941 https://doi.org/10.31857/S0514749221070028.

Dedicated to Doctor of chemical sciences Professor N.V. Zyk on his 80th anniversary

For communication X, see [1].

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Kuznetsov, Y.P., Rasskazova, E.V., Pitushkin, D.A. et al. Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XI. 1-[(Adamantan-1 yl)alkyl]-3-arylselenoureas. Russ J Org Chem 57, 1036–1046 (2021). https://doi.org/10.1134/S1070428021070022

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