Parallel methods for the preparation and SAR exploration of N-ethyl-4-[(8-alkyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-aryl-methyl]-benzamides, powerful mu and delta opioid agonists

Bioorg Med Chem Lett. 2004 Nov 15;14(22):5493-8. doi: 10.1016/j.bmcl.2004.09.004.


Two parallel synthetic methods were developed to explore the structure-activity relationships (SAR) of a series of potent opioid agonists. This series of tropanylidene benzamides proved extremely tolerant of structural variation while maintaining excellent opioid activity. Evaluation of several representative compounds from this series in the mouse hot plate test revealed potent antinociceptive effects upon oral administration.

MeSH terms

  • Analgesics* / chemical synthesis
  • Analgesics* / chemistry
  • Animals
  • Benzamides* / chemical synthesis
  • Benzamides* / chemistry
  • Mice
  • Molecular Structure
  • Pain Measurement / drug effects
  • Receptors, Opioid, delta / agonists*
  • Receptors, Opioid, mu / agonists*
  • Structure-Activity Relationship


  • Analgesics
  • Benzamides
  • Receptors, Opioid, delta
  • Receptors, Opioid, mu