1,3-Disubstituted benzazepines as neuropeptide Y Y1 receptor antagonists

Bioorg Med Chem. 1999 Aug;7(8):1703-14. doi: 10.1016/s0968-0896(99)00087-5.

Abstract

A novel class of potent and selective non-peptide neuropeptide Y (NPY) Y1 receptor antagonists, having benzazepine nuclei, have been designed, synthesized, and evaluated for activity. Through a blind screening we found the compound 1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-7-methoxy-(3-(3)-methyl ureido)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (9: IC50 = 1.6 microM). Chemical modifications of 9 gave a potent NPY Y1 antagonist 3-(N-(4-hydroxyphenyl)-N'-methylguanidino)-1-N-(3-(N'-(tert-butoxy carbonyl)amino)benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (14c: IC5(0=43 nM), which had no affinity for NPY Y2 and Y5 receptors.

MeSH terms

  • Benzazepines / chemistry
  • Benzazepines / pharmacology*
  • Cell Line
  • Magnetic Resonance Spectroscopy
  • Radioligand Assay
  • Receptors, Neuropeptide Y / antagonists & inhibitors*
  • Receptors, Neuropeptide Y / metabolism
  • Structure-Activity Relationship

Substances

  • Benzazepines
  • Receptors, Neuropeptide Y