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Synthesis and properties of 1-[(3-fluoroadamantan-1-yl)methyl]-3-R-ureas and 1,1′-(alkan-1,n-diyl)bis{3-[(3-fluoroadamantan-1-yl)methyl]ureas} as promising soluble epoxide hydrolase inhibitors

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Abstract

A two-step procedure to synthesize (3-fluoroadamantan-1-yl)methyl isocyanate from (3-hydroxyadamantane)acetic acid that involves fluorination with Ishikawa’s reagent on the first step of the synthesis was developed. The reaction of (3-fluoroadamantan-1-yl)methyl isocyanate with aliphatic diamines gave 1,3-disubstituted bis-diureas in 60–97% yields. A strong decrease in the melting points of the obtained ureas (up to ∼70–144 °C) was observed upon introduction of the fluorine atoms at the bridgehead positions of the adamantane unit.

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Authors and Affiliations

  1. Volgograd State Technical University, 28 prosp. Lenina, 400005, Volgograd, Russian Federation

    D. V. Danilov, V. S. D’yachenko, V. V. Burmistrov, G. M. Butov & I. A. Novakov

  2. Volzhsky Polytechnic Institute (branch) of Volgograd State Technical University, 42a ul. Engelsa, 404121, Volzsky of Volgograd Region, Russian Federation

    V. S. D’yachenko & G. M. Butov

Authors
  1. D. V. Danilov
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  2. V. S. D’yachenko
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  3. V. V. Burmistrov
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  4. G. M. Butov
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  5. I. A. Novakov
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Corresponding author

Correspondence to G. M. Butov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 107–113, January, 2022.

This work was performed using the equipment of the Center for Collective Use of Scientific Equipment (CCU) “New Materials and Resource-Saving Technologies” of the National Research Lobachevsky State University of Nizhny Novgorod.

This work was financially supported by the Russian Science Foundation (Project No. 21-73-20123).

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Danilov, D.V., D’yachenko, V.S., Burmistrov, V.V. et al. Synthesis and properties of 1-[(3-fluoroadamantan-1-yl)methyl]-3-R-ureas and 1,1′-(alkan-1,n-diyl)bis{3-[(3-fluoroadamantan-1-yl)methyl]ureas} as promising soluble epoxide hydrolase inhibitors. Russ Chem Bull 71, 107–113 (2022). https://doi.org/10.1007/s11172-022-3383-8

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  • DOI: https://doi.org/10.1007/s11172-022-3383-8

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