Synthesis of 3,8,9-trisubstituted-1,7,9-triaza-fluorene-6-carboxylic acid derivatives as a new class of insulin secretagogues

Bioorg Med Chem. 2007 Sep 1;15(17):5950-64. doi: 10.1016/j.bmc.2007.05.075. Epub 2007 Jun 8.

Abstract

beta-Carbolines stimulate insulin secretion in a glucose-dependent manner, probably by acting on I(3)-binding site. Knowing the in vitro glucose-dependent insulinotropic potential of beta-carbolines, in this project, three series of substituted-triaza-fluorene-6-carboxylic acids (5a-v, 6a-t, and 7a-t) were designed (analogs of beta-carboline) as a new class of insulinotropic agents. The in vitro glucose-dependent insulinotropic activities of test compounds were evaluated using RIN5F assay. Interestingly, with respect to the control, test compounds showed concentration-dependent insulin release, only in presence of glucose load (16.7 mmol). Some of the test compounds from each series were found to be equipotent to standard compound (Harmane), indicating that the pyridine ring systems of substituted-triaza-fluorenes act as bioisosteres of benzene ring in beta-carbolines.

MeSH terms

  • Animals
  • Binding Sites
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / classification
  • Carboxylic Acids / pharmacology*
  • Glucose / pharmacology
  • Insulin / metabolism*
  • Insulin Secretion
  • Molecular Structure
  • Rabbits
  • Radioligand Assay
  • Rats
  • Receptors, Adrenergic, alpha-2 / metabolism
  • Structure-Activity Relationship

Substances

  • Carboxylic Acids
  • Insulin
  • Receptors, Adrenergic, alpha-2
  • Glucose