Synthesis and antidiabetic activity of 3,6,7-trisubstituted-2-(1H-imidazol-2-ylsulfanyl)quinoxalines and quinoxalin-2-yl isothioureas

Arch Pharm (Weinheim). 2007 Jul;340(7):359-66. doi: 10.1002/ardp.200700024.

Abstract

Two series of 3,6,7-trisubstituted-2-(1H-imidazol-2-ylsulfanyl)-quinoxalines 2a-l and 2-(quinoxalin-2-yl)-isothioureas 3a-l were prepared. All the test compounds 2a-l and 3a-l were screened in vitro, in a RIN5F cell-based assay for glucose-dependent insulinotropic activity. A significant concentration and glucose-dependent insulin secretion effect was seen with compounds 2a-l and the insulinotropic activity of compound 2l was found to be identical to that of the standard compound (6,7-dichloro-2-trifluromethyl-3-(5-methyl-1,3,4-thiadiazo-2-ylsulfanyl)-quinoxaline (1)).

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Dose-Response Relationship, Drug
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Imidazoles / pharmacology
  • Insulin / metabolism*
  • Insulin Secretion
  • Insulin-Secreting Cells / drug effects
  • Insulin-Secreting Cells / metabolism
  • Quinoxalines / chemical synthesis*
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry
  • Sulfones / pharmacology
  • Thiourea / analogs & derivatives*
  • Thiourea / chemical synthesis*
  • Thiourea / chemistry
  • Thiourea / pharmacology

Substances

  • Hypoglycemic Agents
  • Imidazoles
  • Insulin
  • Quinoxalines
  • Sulfones
  • Thiourea