Synthesis of novel analogues of the delta opioid ligand SNC-80 using AlCl3-promoted aminolysis

D R Barn; A Bom; J Cottney; W L Caulfield; J R Morphy

doi:10.1016/s0960-894x(99)00174-2

Synthesis of novel analogues of the delta opioid ligand SNC-80 using AlCl3-promoted aminolysis

Bioorg Med Chem Lett. 1999 May 3;9(9):1329-34. doi: 10.1016/s0960-894x(99)00174-2.

Authors

D R Barn¹, A Bom, J Cottney, W L Caulfield, J R Morphy

Affiliation

¹ Organon Laboratories Ltd., Newhouse, Scotland, UK.

PMID: 10340623
DOI: 10.1016/s0960-894x(99)00174-2

Abstract

Two focused libraries of delta opioid ligands were synthesised using AlCl3 facilitated aminolysis. Several compounds were identified with DOR binding affinities higher or similar to SNC-80. A novel acyclic derivative of SNC-80 produced antinociception in the acetic acid abdominal constriction test, which is at least partially mediated via the delta-opioid receptor.

MeSH terms

Aluminum Chloride
Aluminum Compounds / chemistry*
Animals
Benzamides / chemical synthesis*
Chlorides / chemistry*
Inhibitory Concentration 50
Mice
Piperazines / chemical synthesis*
Receptors, Opioid, delta / chemistry*

Substances

Aluminum Compounds
Benzamides
Chlorides
Piperazines
Receptors, Opioid, delta
4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide
Aluminum Chloride