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Synthesis and properties of 1-(3-fluoroadamantan-1-yl)-3-R-ureas and 1,1′-(alkan-1,n-diyl)bis[3-(3-fluoroadamantan-1-yl)ureas], promising inhibitors of epoxide hydrolase sEH.
- Source :
- Russian Chemical Bulletin; Sep2022, Vol. 71 Issue 9, p1998-2005, 8p
- Publication Year :
- 2022
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 10665285
- Volume :
- 71
- Issue :
- 9
- Database :
- Complementary Index
- Journal :
- Russian Chemical Bulletin
- Publication Type :
- Academic Journal
- Accession number :
- 159721701
- Full Text :
- https://doi.org/10.1007/s11172-022-3620-1