Synthesis and biological activities of phenyl piperazine-based peptidomimetic growth hormone secretagogues

Bioorg Med Chem Lett. 1998 Jun 2;8(11):1431-6. doi: 10.1016/s0960-894x(98)00238-8.

Abstract

A new class of potent, orally active phenyl piperazine-based GH secretagogues have been discovered from attempts to mimic the arrangement of the phenyl substituent in the spiroindanyl piperidine and spiroindoline sulfonamide privileged structures of 4 and 1, respectively. The best of these compounds, 18 (EC50 = 2.8 nM) is nearly as potent as MK-0677 for releasing GH from rat pituitary cells.

MeSH terms

  • Animals
  • Cells, Cultured
  • Drug Design
  • Growth Hormone / metabolism*
  • Indoles / pharmacology
  • Molecular Mimicry
  • Peptides / chemistry*
  • Piperazines / chemical synthesis*
  • Piperazines / pharmacology
  • Pituitary Gland / cytology
  • Pituitary Gland / drug effects
  • Pituitary Gland / metabolism
  • Rats
  • Spiro Compounds / pharmacology
  • Stimulation, Chemical
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology

Substances

  • 1-(2-(2-amino-2-methylpropanamido)-5-phenylpentanoyl)-4-(4-(1-methylethylsulfonamido)phenyl)piperazine
  • Indoles
  • Peptides
  • Piperazines
  • Spiro Compounds
  • Sulfonamides
  • Growth Hormone
  • ibutamoren mesylate