Omega-(2-Naphthyloxy) amino alkanes as a novel class of anti-hyperglycemic and lipid lowering agents

Bioorg Med Chem. 2008 Mar 1;16(5):2489-98. doi: 10.1016/j.bmc.2007.11.062. Epub 2007 Nov 28.

Abstract

omega-(2-Naphthyloxy) amino alkanes, obtained as major by-product during course of synthesis of carbamate esters from omega-(2-naphthyloxy) alkyl halides and amines, showed significant anti-hyperglycemic and lipid lowering activities in various test models as a novel class of compounds. Compounds were tested in rat GLM, SLM, STZ, and STZ-S models at 100mg/kg dose. Of these compound 13 was found to be the most active which caused lowering of sugar by 33.6%, 31.0%, 28.5%, and 73.8% in GLM, SLM, STZ, STZ-S, and db/db mice models, respectively. It also significantly effected lowering of LDL in rat model and also in Hamster model without reducing HDL. Most of the compounds showing anti-diabetic and lipid lowering activity have shown promising PPAR-alpha/gamma/delta-activity. Compounds 6, 13, and 19 have shown very good PPAR-alpha/gamma/delta activity.

MeSH terms

  • Alkanes / chemical synthesis*
  • Alkanes / chemistry
  • Alkanes / classification
  • Alkanes / pharmacology*
  • Alkylation
  • Amination
  • Animals
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / classification
  • Hypoglycemic Agents / pharmacology*
  • Hypolipidemic Agents / chemical synthesis*
  • Hypolipidemic Agents / chemistry
  • Hypolipidemic Agents / classification
  • Hypolipidemic Agents / pharmacology*
  • Lipid Metabolism / drug effects
  • Male
  • Molecular Structure
  • Naphthalenes / chemistry*
  • PPAR gamma / metabolism
  • Rats
  • Structure-Activity Relationship

Substances

  • Alkanes
  • Hypoglycemic Agents
  • Hypolipidemic Agents
  • Naphthalenes
  • PPAR gamma