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Synthesis and evaluation of the beta-turn properties of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones and of their spirocyclic derivative.

  • June 8, 2006

A series of 4‐amino‐tetrahydro‐2‐benzazepin‐3‐one derivatives (Ac–Aba–Xxx–NHMe) were prepared as tetrapeptide mimetics. Considering the structural resemblance with the so‐called Freidinger lactams, their propensity to adopt a β‐turn conformation was investigated by NMR spectroscopy (solvent and temperature dependence) and molecular modeling. Interestingly, most of these lactams adopt extended conformations, only the spiro‐benzazepinone 9 has a strong preference for the formation of a β‐turn.

 

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