Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction

Design, Synthesis, and Biological Evaluation of (+)‐Camphor‐ and (−)‐Fenchone‐Based Derivatives as Potent Orthopoxvirus Inhibitors

“…(1R,4R)‐1,7,7‐Trimethylbicyclo[2.2.1]heptan–2‐one oxime ( 4 a ), [37] (1R,2R,4R)‐1,7,7‐trimethylbicyclo[2.2.1]heptan–2‐amine ( exo ‐bornylamine 5 a ), [38] (1R,2S,4R)‐1,7,7‐trimethylbicyclo[2.2.1]heptan–2‐amine ( endo ‐bornylamine 5 b ), [39] (1R,4S)‐1,3,3‐trimethylbicyclo[2.2.1]heptan–2‐one oxime ( 4 b ), [23] (1R,2S,4S)‐1,3,3‐trimethylbicyclo[2.2.1]heptan–2‐amine ( 6 a ) and (1R,2R,4S)‐1,3,3‐trimethylbicyclo[2.2.1]heptan–2‐amine ( 6 b ), [23] ((1R,4R)‐1,7,7‐trimethylbicyclo[2.2.1]heptan–2‐ylidene)hydrazine [19] ( 1 a ) and ((1R,4S)‐1,3,3‐trimethylbicyclo[2.2.1]heptan–2‐ylidene)hydrazine [20] ( 1 b ) were prepared according to the procedure reported in the literature from purchased (+)‐camphor and (−)‐fenchone.…”

Bioisosteric substitution of adamantane with bicyclic lipophilic groups improves water solubility of human soluble epoxide hydrolase inhibitors

“…Reaction of either bicyclic isocyanates 14 with amines of bicyclic amines 15 with isocyanates were used to synthesize ureas 1a, 1b, 2a, 2b, 2d, 2e and 3a-c (Scheme 1). Furan-2ylmethanamine was used for compound 2c.…”

Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: V. 1-(Bicyclo[2.2.1]heptan-2-yl)-3-R- and 1-(1,7,7-Tricyclo[2.2.1]heptan-2-yl)-3-R-ureas

“…2-Fluoroaniline (≥ 99%, CAS 348-54-9), 1,6-diaminohexane (98%, CAS 124-09-4), 1-aminomethyladamantane (98%, CAS 17768-41-1), triethylamine (BioUltra ≥ 99.5%, CAS 121-44-8), DMF (anhydrous 99.8%, CAS 68-12-2) were purchased from Sigma–Aldrich and used as received. trans -[4-(Aminocyclohexyl)oxy]benzoic acid [ 3 ], 1-(4-aminopiperidin-1-yl)propan-1-one [US2013143925], bicyclo[2.2.1]heptan-2-amine [ 22 ], and 1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine [ 22 ] were prepared by known procedures.…”