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Synthesis and Properties of N,N′-Disubstituted Ureas Containing Adamantane and Pyridine (Quinoline) Fragments

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Abstract

A series of N,N′-disubstituted ureas containing a pyridine or quinoline fragment and a lipophilic adamantane moiety (13 examples, 53–94% yield) have been synthesized by the reaction of N,N-dimethyl-N′-(pyridin-2-yl or quinoline-2-yl)ureas with amine hydrochlorides. The synthesized compounds differed from each other by the position of substitution in the adamantane fragment, structure of the alkyl linker between the adamantane fragment and amide group, and heterocyclic substituent. They are potential target-oriented inhibitors of human soluble epoxide hydrolase (sEH).

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ACKNOWLEDGMENTS

This study was performed using the equipment of the Magnetic Resonance Research Center and Chemical Analysis and Materials Research Center at the St. Petersburg State University.

Funding

This work was financially supported by the Russian Science Foundation (project no. 19-13-00008).

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Authors and Affiliations

  1. St. Petersburg State University, 199034, St. Petersburg, Russia

    S. O. Baykova, S. V. Baykov, A. A. Petrov & V. P. Boyarskiy

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

    V. V. Burmistrov

Authors
  1. S. O. Baykova
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  2. S. V. Baykov
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  3. A. A. Petrov
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  4. V. V. Burmistrov
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  5. V. P. Boyarskiy
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Corresponding authors

Correspondence to A. A. Petrov or V. P. Boyarskiy.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 7, pp. 910–919 https://doi.org/10.31857/S0514749223070054.

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Baykova, S.O., Baykov, S.V., Petrov, A.A. et al. Synthesis and Properties of N,N′-Disubstituted Ureas Containing Adamantane and Pyridine (Quinoline) Fragments. Russ J Org Chem 59, 1149–1157 (2023). https://doi.org/10.1134/S1070428023070059

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  • DOI: https://doi.org/10.1134/S1070428023070059

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