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Synthesis and inhibitory activity of 1,3-(adamantan-1(2)-yl)- imidazolidine-2,4,5-triones and 3,3'-(adamantan-1-yl)- bis(1-alkylimidazolidine-2,4,5-triones)

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Chemistry of Heterocyclic Compounds Aims and scope

A series of 1,3-(adamantan-1(2)-yl)imidazolidine-2,4,5-triones and 1,1'-(alkane-1,n-diyl)bis[3-(adamantan-1-yl)imidazolidine-2,4,5-triones] was synthesized via cyclization of 1,3-bis[adamantan-1(2)-ylureas] and 1,1'-(alkyl-1,n-diyl)bis[3-(adamantan-1-yl)ureas] with oxalyl chloride under mild conditions with high yields. All synthesized compounds were tested in vitro as inhibitors of soluble human epoxide hydrolase. A number of compounds have high inhibitory activity (IC50 1.6–650 nM), which makes them promising inhibitors of soluble epoxide hydrolase.

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This work was supported by the Russian Foundation for Basic Research (Regions) (grant 16-43-340116, р_а) and the Ministry of Education and Science of the Russian Federation within the framework of the baseline of the State Assignment for 2017-2019 (project 4.7491.2017/BCh). Equipment was purchased under the strategic development program of Volgograd State Technical University for 2012-2016.

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Authors and Affiliations

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

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

  2. Department of Biology, Faculty of Science, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime, 790-8566, Japan

    Kosuke Nishi & In-Hae Kim

Authors
  1. Vladimir S. D’yachenko
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  2. Vladimir V. Burmistrov
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  3. Kosuke Nishi
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  4. In-Hae Kim
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  5. Gennady M. Butov
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Correspondence to Gennady M. Butov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1080–1083

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D’yachenko, V.S., Burmistrov, V.V., Nishi, K. et al. Synthesis and inhibitory activity of 1,3-(adamantan-1(2)-yl)- imidazolidine-2,4,5-triones and 3,3'-(adamantan-1-yl)- bis(1-alkylimidazolidine-2,4,5-triones). Chem Heterocycl Comp 53, 1080–1083 (2017). https://doi.org/10.1007/s10593-017-2174-x

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  • DOI: https://doi.org/10.1007/s10593-017-2174-x

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