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Synthesis and properties of 1-[(adamantan-1-yl)methyl]-3-pyrazolyl ureas

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Chemistry of Heterocyclic Compounds Aims and scope

A series of 1,3-disubstituted ureas containing 1,3,5-trisubstituted pyrazole and (adamantan-1-yl)methyl fragments were synthesized in the reaction of 1-(isocyanatomethyl)adamantane with 3- or 4-aminopyrazoles under mild conditions in 67-92% yields. The inhibitory activity of the obtained compounds with respect to human soluble epoxide hydrolase (sEH) was 16.2-50.2 nmol/l, with solubility in water of 45-85 μmol/l.

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The work was supported by the Ministry of Education and Science of the Russian Federation within the framework of the Basic part of the State assignment for 2017-2019 (No.4.7491.2017/CU) for V.S.D., D.V.D., V.V.B., G.M.B.

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Authors and Affiliations

  1. Volzhsky Polytechnic Institute (branch) of the Volgograd State Technical University, 42a Engelsa St, Volzhsky, 404121, Russia

    Vladimir S. D’yachenko, Dmitry V. Danilov, Vladimir V. Burmistrov & Gennady M. Butov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991, Russia

    Tatyana K. Shkineva & Irina А. Vatsadze

Authors
  1. Vladimir S. D’yachenko
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  2. Dmitry V. Danilov
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  3. Tatyana K. Shkineva
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  4. Irina А. Vatsadze
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  5. Vladimir V. Burmistrov
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  6. Gennady M. Butov
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Correspondence to Gennady M. Butov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(2), 129-134

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D’yachenko, V.S., Danilov, D.V., Shkineva, T.K. et al. Synthesis and properties of 1-[(adamantan-1-yl)methyl]-3-pyrazolyl ureas. Chem Heterocycl Comp 55, 129–134 (2019). https://doi.org/10.1007/s10593-019-02428-2

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  • DOI: https://doi.org/10.1007/s10593-019-02428-2

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