Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 7: syntheses and opioid receptor properties of cyclic variants of cyclazocine

Bioorg Med Chem Lett. 2009 Jan 15;19(2):365-8. doi: 10.1016/j.bmcl.2008.11.076. Epub 2008 Nov 24.

Abstract

A series of 7,8- and 8,9-fused triazole and imidazole analogues of cyclazocine have been made and characterized in opioid receptor binding and [(35)S]GTPgammaS assays. Target compounds were designed to explore the SAR surrounding our lead molecule for this study, namely the 8,9-fused pyrrolo analogue 2 of cyclazocine. Compared to 2, many of the new compounds in this study displayed very high affinity for opioid receptors.

Publication types

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

MeSH terms

  • Animals
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Cyclazocine / analogs & derivatives
  • Cyclazocine / chemical synthesis*
  • Cyclazocine / metabolism
  • Cyclazocine / pharmacology*
  • Cyclization
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • Radioligand Assay
  • Receptors, Opioid / drug effects*
  • Receptors, Opioid / metabolism
  • Structure-Activity Relationship
  • Sulfur Radioisotopes

Substances

  • Receptors, Opioid
  • Sulfur Radioisotopes
  • Guanosine 5'-O-(3-Thiotriphosphate)
  • Cyclazocine