NMR and molecular modelling based conformational analysis of some N-alkyl 1- and 2-benzazepinones: useful central nervous system agent design motifs.
Variable temperature 1H NMR lineshape analyses and 13C NMR spin-lattice relaxation time studies were undertaken to characterise the conformationally dynamic N-alkyl 1- and 2-benzazepinones 1 and 2. For 1, dynamic interchange between two mirror-image puckered forms of the azepine ring occurs with a barrier of 56 kJ mol-1. There is a significantly greater degree of ring flexibility in the case of 2. Molecular modelling studies were used to examine the degree of sidechain flexibility in these compounds.
Nicholls
I A
IA
School of Pharmaceutical Chemistry, Victorian College of Pharmacy, Monash University, Parkville, Victoria, Australia.
Craik
D J
DJ
Alewood
P F
PF
D001552:Benzazepines / Q000737:chemistry* / Q000494:pharmacology; D002490:Central Nervous System / Q000187:drug effects*; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation
D001552:Benzazepines