Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 7: syntheses and opioid receptor properties of cyclic variants of cyclazocine.
A series of 7,8- and 8,9-fused triazole and imidazole analogues of cyclazocine have been made and characterized in opioid receptor binding and [(35)S]GTPgammaS assays. Target compounds were designed to explore the SAR surrounding our lead molecule for this study, namely the 8,9-fused pyrrolo analogue 2 of cyclazocine. Compared to 2, many of the new compounds in this study displayed very high affinity for opioid receptors.
Wentland
Mark P
MP
Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, 110 8th St., Troy, NY 12180, USA. wentmp@rpi.edu
Lu
Qun
Q
Ganorkar
Rakesh
R
Zhang
Shao-Zhong
SZ
Jo
Sunjin
S
Cohen
Dana J
DJ
Bidlack
Jean M
JM
D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D003496:Cyclazocine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D003500:Cyclization; D016244:Guanosine 5'-O-(3-Thiotriphosphate) / Q000378:metabolism; D011869:Radioligand Assay; D011957:Receptors, Opioid / Q000187:drug effects* / Q000378:metabolism; D013329:Structure-Activity Relationship; D013462:Sulfur Radioisotopes
D011957:Receptors, Opioid; D013462:Sulfur Radioisotopes; D016244:Guanosine 5'-O-(3-Thiotriphosphate); D003496:Cyclazocine