Synthesis and Evaluation of the β-Turn Properties of 4-Amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones and of Their Spirocyclic Derivative

✍ Scribed by Karolien Van Rompaey; Steven Ballet; Csaba Tömböly; Rien De Wachter; Kenno Vanommeslaeghe; Monique Biesemans; Rudolph Willem; Dirk Tourwé

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 246 KB
• Volume: 2006
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200500996

✦ Synopsis

Abstract

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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)