Synthesis and Properties of N , N ′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XII. N -(1,3,3-Trimethylbicyclo[2.2.1]heptan-2-yl)- N ′-R-ureas and -thioureas

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY(2022)

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摘要
N , N ′-Disubstituted ureas and thioureas containing a lipophilic optically active bicyclic fragment of natural origin were synthesized by reaction of ( R )- and ( S )-1,3,3-trimethylbicyclo[2.2.1]heptan-2-amine (prepared from the natural terpenoid fenchone) with aromatic isocyanates and isothiocyanates in up to 88 and 87% yield, respectively, with the goal of assessing the enantiomeric specificity of human soluble epoxide hydrolase (hsEH). The synthesized compounds were found to be promising as inhibitors of RNA virus replication and hsEH.
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natural compounds, bicyclo[2, 2, 1]heptane, isocyanate, isothiocyanate, urea, fenchone, soluble epoxide hydrolase, optical isomerism, racemate
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