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Synthesis and properties of diadamantyl-containing symmetric diureas as target-oriented inhibitors of human soluble epoxide hydrolase

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Abstract

A series of target-oriented competitive inhibitors of human soluble epoxide hydrolase have been synthesized. The compounds retain the inhibitory properties at concentrations down to 4 nM. Based on the results of molecular modeling, it has been shown that the high inhibitory activity of this series of compounds is achieved by a unique mode of the binding to the active site of the enzyme.

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Abbreviations

ACPU:

1-(adamant-1-yl)-3-(1-(2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetyl)piperidin-4-yl)urea

AEPU:

1-(adamant-1-yl)-3-(1-acetylpiperidin-4-yl) urea

CMNPC:

cyano(2-methoxynaphthalen-6-yl)methyl-trans-(3-phenyloxyran-2-yl)methyl carbonate

sEH:

soluble epoxide hydrolase

t-AUCB:

trans-4-[(4-(3-(adamant-1-yl)ureido)-cyclohexyl)oxy]-benzoic acid

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Authors and Affiliations

  1. Volzhskii Polytechnical Institute (Branch), Volgograd State Technical University, ul. Engelsa 42a, Volzhskii, 404121, Russia

    V. V. Burmistrov & G. M. Butov

  2. Department of Chemistry, Moscow State University, Moscow, 119991, Russia

    D. S. Karlov, V. A. Palyulin & N. S. Zefirov

  3. Department of Entomology and Nematology and UC Davis Comprehensive Cancer Center, University of California, Davis, CA, 95616, USA

    C. Morisseau & B. D. Hammock

  4. ISCALARE Laboratory, Moscow Institute of Physics and Technology (State University), Dolgoprudnyi, Moscow oblast, 141701, Russia

    D. S. Karlov

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  1. V. V. Burmistrov
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Correspondence to G. M. Butov.

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Original Russian Text © V.V. Burmistrov, G.M. Butov, D.S. Karlov, V.A. Palyulin, N.S. Zefirov, C. Morisseau, B.D. Hammock, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 4, pp. 448–459.

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Burmistrov, V.V., Butov, G.M., Karlov, D.S. et al. Synthesis and properties of diadamantyl-containing symmetric diureas as target-oriented inhibitors of human soluble epoxide hydrolase. Russ J Bioorg Chem 42, 404–414 (2016). https://doi.org/10.1134/S1068162016030067

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