Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs

Org Biomol Chem. 2010 May 7;8(9):2252-9. doi: 10.1039/c001307b. Epub 2010 Mar 16.

Abstract

The GPR30 agonist probe G-1 and structural analogs were efficiently synthesized using multicomponent or stepwise Sc(III)-catalyzed aza-Diels-Alder cyclization. Optimization of solvent and reaction temperature provided enhanced endo-diastereoselectivity.

Publication types

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

MeSH terms

  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry
  • Cyclopentanes / pharmacology*
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • Receptors, G-Protein-Coupled / agonists*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 1-(4-(6-bromobenzo(1,3)dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta(c)quinolin-8-yl)ethanone
  • Cyclopentanes
  • Quinolines
  • Receptors, G-Protein-Coupled
  • 1,2,3,4-tetrahydroquinoline