Potent MCH-1 receptor antagonists from cis-1,4-diaminocyclohexane-derived indane analogs

Bioorg Med Chem Lett. 2013 Jul 15;23(14):4216-20. doi: 10.1016/j.bmcl.2013.05.017. Epub 2013 May 15.

Abstract

Benzimidazole and indane are the two key fragments in our potent and selective MCH-1 receptor (MCHR1) antagonists. To identify novel linkers connecting the two fragments, we investigated diamino-cycloalkane-derived analogs and discovered highly potent antagonists with cis-1,4-diaminocyclohexane as a unique spacer in this chemical class. Structural overlay suggested that cis-1-substituted-4-aminocyclohexane functions as a bioisostere of 4-substituted-piperidine and that the active conformation adopts a U-shaped orientation.

MeSH terms

  • Animals
  • Benzimidazoles / chemistry
  • Cyclohexanes / chemistry*
  • Half-Life
  • Indans / chemistry*
  • Indans / metabolism
  • Indans / pharmacokinetics
  • Isomerism
  • Mice
  • Protein Binding
  • Rats
  • Receptors, Pituitary Hormone / antagonists & inhibitors*
  • Receptors, Pituitary Hormone / metabolism

Substances

  • Benzimidazoles
  • Cyclohexanes
  • Indans
  • Receptors, Pituitary Hormone
  • melanin-concentrating hormone receptor
  • Cyclohexane
  • benzimidazole
  • indan