Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 4. Opioid receptor binding properties of 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogues of cyclazocine and ethylketocycalzocine.
The synthesis and evaluation of a series of aryl-containing N-monosubstituted analogues of the lead compound 8-carboxamidocyclazocine were performed to probe a putative hydrophobic binding pocket of opioid receptors. High binding affinity to mu, kappa, and delta opioid receptors was observed for the 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogue.
Wentland
Mark P
MP
Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, New York 12180, USA. wentmp@rpi.edu
VanAlstine
Melissa
M
Kucejko
Robert
R
Lou
Rongliang
R
Cohen
Dana J
DJ
Parkhill
Amy L
AL
Bidlack
Jean M
JM
D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D003496:Cyclazocine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D016314:Ethylketocyclazocine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D011869:Radioligand Assay; D017465:Receptors, Opioid, delta / Q000187:drug effects* / Q000378:metabolism; D017473:Receptors, Opioid, kappa / Q000187:drug effects* / Q000378:metabolism; D017450:Receptors, Opioid, mu / Q000187:drug effects* / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C514073:3-(cyclopropylmethyl)-6-ethyl-1,2,3,4,5,6-hexahydro-11-methyl-N-(2-(1,1'-biphenyl)-4-ylethyl)-1-oxo-2,6-methano-3-benazocine-8-carboxamide; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; D016314:Ethylketocyclazocine; D003496:Cyclazocine