Discovery of (S)-2-cyclopentyl-N-((1-isopropylpyrrolidin2-yl)-9-methyl-1-oxo-2,9-dihydro-1H-pyrrido[3,4-b]indole-4-carboxamide (VU0453379): a novel, CNS penetrant glucagon-like peptide 1 receptor (GLP-1R) positive allosteric modulator (PAM)

J Med Chem. 2014 Dec 11;57(23):10192-7. doi: 10.1021/jm501375c. Epub 2014 Dec 2.

Abstract

A duplexed, functional multiaddition high throughput screen and subsequent iterative parallel synthesis effort identified the first highly selective and CNS penetrant glucagon-like peptide-1R (GLP-1R) positive allosteric modulator (PAM). PAM (S)-9b potentiated low-dose exenatide to augment insulin secretion in primary mouse pancreatic islets, and (S)-9b alone was effective in potentiating endogenous GLP-1R to reverse haloperidol-induced catalepsy.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allosteric Regulation / drug effects
  • Animals
  • Catalepsy / chemically induced
  • Catalepsy / drug therapy
  • Central Nervous System Agents / therapeutic use
  • Drug Synergism
  • Exenatide
  • Glucagon-Like Peptide 1 / pharmacology
  • Glucagon-Like Peptide-1 Receptor
  • Haloperidol
  • High-Throughput Screening Assays
  • Indoles / chemical synthesis*
  • Indoles / metabolism
  • Indoles / pharmacokinetics
  • Indoles / pharmacology
  • Insulin / metabolism
  • Insulin Secretion
  • Islets of Langerhans / drug effects
  • Male
  • Mice, Inbred C57BL
  • Microsomes, Liver / metabolism
  • Peptides / pharmacology
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / metabolism
  • Pyrrolidines / pharmacokinetics
  • Pyrrolidines / pharmacology
  • Receptors, Glucagon / drug effects*
  • Structure-Activity Relationship
  • Venoms / pharmacology

Substances

  • (S)-2-cyclopentyl-N-((1-isopropylpyrrolidin2-yl)-9-methyl-1-oxo-2,9-dihydro-1H-pyrrido(3,4-b)indole-4-carboxamide
  • Central Nervous System Agents
  • Glp1r protein, mouse
  • Glucagon-Like Peptide-1 Receptor
  • Indoles
  • Insulin
  • Peptides
  • Pyrrolidines
  • Receptors, Glucagon
  • Venoms
  • Glucagon-Like Peptide 1
  • Exenatide
  • Haloperidol