Highly constrained dipeptoid analogues containing a type II' beta-turn mimic as novel and selective CCK-A receptor ligands

Bioorg Med Chem Lett. 1999 Jan 4;9(1):43-8. doi: 10.1016/s0960-894x(98)00677-5.

Abstract

Conformationally constrained dipeptoid analogues containing the type II' beta-turn mimic (2S,5s,11bR)-2-amino-3-oxohexahydroindolizino[8,7-b]indole-5 -carboxylate framework in place of the alpha-MeTrp residue, show high binding affinity and selectivity for CCK-A receptors, suggesting that a turn-like conformation could contribute to the bioactive conformation at this CCK receptor subtype.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites
  • Brain / metabolism
  • Drug Evaluation, Preclinical
  • Guinea Pigs
  • Ileum / drug effects
  • Ileum / metabolism
  • Indoles / chemistry*
  • Indoles / metabolism
  • Indoles / pharmacology*
  • Indolizines / chemistry*
  • Indolizines / metabolism
  • Indolizines / pharmacology*
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Mimicry
  • Molecular Structure
  • Pancreas / metabolism
  • Peptides / chemistry*
  • Peptides / metabolism*
  • Peptides / pharmacology
  • Rats
  • Receptor, Cholecystokinin A
  • Receptor, Cholecystokinin B
  • Receptors, Cholecystokinin / agonists
  • Receptors, Cholecystokinin / antagonists & inhibitors*
  • Receptors, Cholecystokinin / metabolism*
  • Sincalide / metabolism

Substances

  • 2-((benzyloxycarbonyl)amino)-1,3a,4,5,10,10a-hexahydro-4-(1-phenylmethyl-2-carboxyethyl)indolo(3,2-e)indolizine-3(2H)-one
  • Indoles
  • Indolizines
  • Peptides
  • Receptor, Cholecystokinin A
  • Receptor, Cholecystokinin B
  • Receptors, Cholecystokinin
  • Sincalide