Journal
RUSSIAN CHEMICAL BULLETIN
Volume 71, Issue 9, Pages 1998-2005Publisher
SPRINGER
DOI: 10.1007/s11172-022-3620-1
Keywords
adamantane; isocyanate; fluorine; fluoroadamantane; soluble epoxide hydrolase; hsEH
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Funding
- N. I. Lobachevsky Nizhny Novgorod State University
- Russian Science Foundation [21-73-20123]
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A method for the synthesis of 3-fluoro-1-isocyanatoadamantane and a new series of inhibitors were developed. The absence of a methylene bridge between adamantane and urea led to higher melting points, while the introduction of a fluorine atom reduced melting points.
A three-stage method for the preparation of 3-fluoro-1-isocyanatoadamantane in 76% yield was developed using the reaction of 3-hydroxyadamantane-1-carboxylic acid with Ishikawa's reagent and subsequent reaction with diphenylphosphoryl azide. The reaction of 3-fluoro-1-isocyanatoadamantane with a number of aliphatic diamines, fluorine-containing anilines, and trans-4-amino(cyclohexyloxy)benzoic acid afforded a new series of targeted inhibitors of epoxide hydrolase sEH in 43-89% yields. The absence of a methylene bridge between the adamantane and urea moieties led to an increase in the melting points of the synthesized compounds, while the introduction of a fluorine atom reduces their melting points compared to nonfluorinated analogs.
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