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Synthesis and Properties of N-(R-Adamantan-1-ylalkyl)-N′-[3(4)-fluorophenyl]thioureas—Target-Oriented Human Soluble Epoxide Hydrolase (hsEH) Inhibitors

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Abstract

Reactions of 3(4)-fluorophenyl isothiocyanates with amines of the adamantane series in DMF afforded 86–93% of the corresponding N,N′-disubstituted thioureas that are target-oriented inhibitors of human soluble epoxide hydrolase (hsEH). The effect of isosteric replacement of hydrogen in the aromatic fragment by fluorine and of oxygen in the urea fragment by sulfur on the IC50 value was estimated. The inhibitory activity increases twofold for the 3-fluorophenyl derivatives and ninefold for 4-fluorophenyl analogs.

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Authors and Affiliations

  1. Volzhsky Polytechnic Institute (Branch), Volgograd State Technical University, ul. Engel’sa 42a, Volzhsky, Volgograd oblast, 404121, Russia

    D. A. Pitushkin, V. V. Burmistrov & G. M. Butov

  2. Volgograd State Technical University, pr. imeni Lenina 28, Volgograd, 400005, Russia

    G. M. Butov

Authors
  1. D. A. Pitushkin
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  2. V. V. Burmistrov
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  3. G. M. Butov
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Corresponding author

Correspondence to G. M. Butov.

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Original Russian Text © D.A. Pitushkin, V.V. Burmistrov, G.M. Butov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 10, pp. 1457–1462.

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Pitushkin, D.A., Burmistrov, V.V. & Butov, G.M. Synthesis and Properties of N-(R-Adamantan-1-ylalkyl)-N′-[3(4)-fluorophenyl]thioureas—Target-Oriented Human Soluble Epoxide Hydrolase (hsEH) Inhibitors. Russ J Org Chem 54, 1469–1474 (2018). https://doi.org/10.1134/S1070428018100056

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  • DOI: https://doi.org/10.1134/S1070428018100056

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