title: 3-Carboxamido analogues of morphine and naltrexone. synthesis and opioid receptor binding properties.
abstract: In response to the unexpectedly high affinity for opioid receptors observed in a novel series of cyclazocine analogues where the prototypic 8-OH was replaced by a carboxamido group, we have prepared the corresponding 3-CONH(2) analogues of morphine and naltrexone. High affinity (K(i)=34 and 1.7nM) for mu opioid receptors was seen, however, the new targets were 39- and 11-fold less potent than morphine and naltrexone, respectively.
authors: Department of Chemistry, Rensselaer Polytechnic Institute, 110 8th Street, 12180, Troy, NY, USA. wentmp@rpi.edu
authors: M P
authors: MP
authors: Wentland
authors: R
authors: R
authors: Lou
authors: C M
authors: CM
authors: Dehnhardt
authors: W
authors: W
authors: Duan
authors: D J
authors: DJ
authors: Cohen
authors: J M
authors: JM
authors: Bidlack
mesh_terms: D000577:Amides / Q000737:chemistry*; D009022:Morphine Derivatives / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D009271:Naltrexone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D011485:Protein Binding; D011957:Receptors, Opioid / Q000378:metabolism*
chemical_list: D000577:Amides; D009022:Morphine Derivatives; D011957:Receptors, Opioid; D009271:Naltrexone