Stereochemistry of novel delta selective opiate antagonists.
We have discovered novel delta selective opiate antagonists of a non-peptide nature. Our lead compound at the present time is the mixed azine between estrone and naloxone, the compound named EH-NAL. In this paper we describe the stereochemistry of EH-NAL and an EH-NAL analog, the mixed azine between pregnenolone and naltrexone, the compound named PH-NX. The stereochemical assignments are based on the high-resolution 13C-NMR studies and on the X-ray structural determinations.
Kolb
V M
VM
Department of Chemistry, University of Wisconsin-Parkside, Kenosha 53141.
Hua
D H
DH
Duax
W L
WL
D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009270:Naloxone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009271:Naltrexone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D011284:Pregnenolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D011957:Receptors, Opioid / Q000187:drug effects*; D017465:Receptors, Opioid, delta; D014961:X-Ray Diffraction
D011957:Receptors, Opioid; D017465:Receptors, Opioid, delta; C054867:pregnenolone-naltrexone azine; D004970:Estrone; D009270:Naloxone; D009271:Naltrexone; D011284:Pregnenolone; C054866:estrone-naloxone azine