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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 2, pp 129–134 | Cite as

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

  • Vladimir S. D’yachenko
  • Dmitry V. Danilov
  • Tatyana K. Shkineva
  • Irina А. Vatsadze
  • Vladimir V. Burmistrov
  • Gennady M. ButovEmail author
Article
  • 43 Downloads

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.

Keywords

adamantane derivatives amines 1,3-disubstituted ureas isocyanates pyrazoles soluble epoxide hydrolase (sEH) inhibitors 

Notes

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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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Vladimir S. D’yachenko
    • 1
  • Dmitry V. Danilov
    • 1
  • Tatyana K. Shkineva
    • 2
  • Irina А. Vatsadze
    • 2
  • Vladimir V. Burmistrov
    • 1
  • Gennady M. Butov
    • 1
    Email author
  1. 1.Volzhsky Polytechnic Institute (branch) of the Volgograd State Technical UniversityVolzhskyRussia
  2. 2.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia

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