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

Karolien Van Rompaey, Steven Ballet, C. Tömböly, Rien De Wachter, Kenno Vanommeslaeghe, Monique Biesemans, Rudolph Willem, Dirk Tourwé

Research output: Contribution to journalArticle

26 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2899-2911
Number of pages13
JournalEuropean Journal of Organic Chemistry
Issue number13
DOIs
Publication statusPublished - Jun 26 2006

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Lactams
Conformations
Derivatives
Molecular modeling
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Temperature
4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one

Keywords

  • Asymmetric synthesis
  • Conformation analysis
  • Lactams
  • Molecular modeling

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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. / Van Rompaey, Karolien; Ballet, Steven; Tömböly, C.; De Wachter, Rien; Vanommeslaeghe, Kenno; Biesemans, Monique; Willem, Rudolph; Tourwé, Dirk.

In: European Journal of Organic Chemistry, No. 13, 26.06.2006, p. 2899-2911.

Research output: Contribution to journalArticle

Van Rompaey, Karolien ; Ballet, Steven ; Tömböly, C. ; De Wachter, Rien ; Vanommeslaeghe, Kenno ; Biesemans, Monique ; Willem, Rudolph ; Tourwé, Dirk. / 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. In: European Journal of Organic Chemistry. 2006 ; No. 13. pp. 2899-2911.
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