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Synthesis and properties of 1-(R-adamant-1-yl)-3-(1-propionylpiperidin-4-yl)ureas and 4-({4-[3-(R-adamant-1-yl)ureido]cyclohexyl}oxy)benzoic acids, efficient target-oriented human soluble epoxide hydrolase inhibitors

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Abstract

A reaction of R-adamant-1-yl isocyanates with 4-[(4-aminocyclohexyl)oxy]benzoic acid and 1-(4-aminopiperidin-1-yl)propan-1-one in DMF afforded corresponding ureas in 90—95% yield, the target-oriented inhibitors of epoxide hydrolase sEH. The ureas are characterized by reduced melting points and increased solubility in water, as well as by inhibitory activity in the range of 0.5—4.0 nmol L–1.

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Authors and Affiliations

  1. Volzhsky Polytechnical Institute (branch) of the Volgograd State Technical University, 42a ul. Engelsa, 404121, Volzhsky, Russian Federation

    G. M. Butov, V. V. Burmistrov & D. V. Danilov

Authors
  1. G. M. Butov
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  2. V. V. Burmistrov
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  3. D. V. Danilov
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Correspondence to G. M. Butov.

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Based on the Materials of the Interdisciplinary Symposium "MOBI-ChemPharma 2017" (May 28—31, 2017, Sevastopol, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1876—1880, October, 2017.

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Butov, G.M., Burmistrov, V.V. & Danilov, D.V. Synthesis and properties of 1-(R-adamant-1-yl)-3-(1-propionylpiperidin-4-yl)ureas and 4-({4-[3-(R-adamant-1-yl)ureido]cyclohexyl}oxy)benzoic acids, efficient target-oriented human soluble epoxide hydrolase inhibitors. Russ Chem Bull 66, 1876–1880 (2017). https://doi.org/10.1007/s11172-017-1961-y

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  • DOI: https://doi.org/10.1007/s11172-017-1961-y

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