Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: I. Synthesis of 1-(Adamantan-1-yl)-3-(fluoro, chlorophenyl)ureas

1-(3-Chlorophenyl)-3-(6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexyl)thiourea

“…Previously, we have observed synthesis and inhibitory activity against human soluble epoxide hydrolase (sEH) of multiple series of adamantyl-containing 1,3-disubstituted ureas and thioureas, and the same findings have been reported by our colleagues [1][2][3]. sEH is involved in the metabolism of epoxy fatty acids to corresponding vicinal diols through a catalytic addition of water [4,5].…”

N-Substituted S-Alkyl Carbamothioates in the Synthesis of Nitrogen-containing Functional Derivatives of the Adamantane Series

“…Isocyanates are commonly prepared by phosgenation of amines or by Curtius rearrangement from acyl azides [ 25 ]. Most of the methods for the preparation of adamantan-1-yl isocyanate include the aforementioned treatment of 1-aminoadamantane hydrochloride with phosgene [ 26 , 27 ] or triphosgene [ 28 ] and the implementation of Curtius rearrangement [ 29 ], including with the preliminary preparation of 1-azidoadamantane from adamantane-1-carboxylic acid [ 13 , 30 ] or its acid chloride [ 31 – 35 ]. Alternative synthetic approaches to adamantan-1-yl isocyanate involve the cleavage of 1,3-dehydroadamantane in sulfuric acid in the presence of sodium cyanate [ 36 ], the reaction of 1-bromoadamantane with the silver salt of nitrocyanamide [ 37 ], and thermolysis of 2-(adamantan-1-yl)-5-methyl-1,3-oxothiolane [ 38 ].…”

Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: IV.1 1-(Bicyclo[2.2.1]hept-5-en-2-yl)-3-(fluoro, chlorophenyl)ureas

“…Comparing the melting point of compound 4c with those of its adamantane analogs we can note that the bicyclo[2.2.1]hept-5-enyl fragment decreases the melting point by 27°С compared to the adamantyl [ 20 ] and by 56°С compared to the 4-oxoadamantyl fragments [ 23 ].…”