3-Carboxamido analogues of morphine and naltrexone. synthesis and opioid receptor binding properties.
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.
Wentland
M P
MP
Department of Chemistry, Rensselaer Polytechnic Institute, 110 8th Street, 12180, Troy, NY, USA. wentmp@rpi.edu
Lou
R
R
Dehnhardt
C M
CM
Duan
W
W
Cohen
D J
DJ
Bidlack
J M
JM
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*
D000577:Amides; D009022:Morphine Derivatives; D011957:Receptors, Opioid; D009271:Naltrexone