2 beta-substituted analogues of cocaine. Synthesis and inhibition of binding to the cocaine receptor.
The potencies of a series of 2 beta-substituted cocaine analogues to displace [3H]-3 beta-(p-fluorophenyl)tropane-2 beta-carboxylic acid methyl ester binding in rat striatal membranes demonstrate the requirement for a 2 beta-substituent with two hydrogen-bond acceptors. The insensitivity of the ester moiety to steric and electronic factors suggests its modification to provide site-specific irreversible ligands.
Lewin
A H
AH
Research Triangle Institute, Research Triangle Park, North Carolina 27709.
Gao
Y G
YG
Abraham
P
P
Boja
J W
JW
Kuhar
M J
MJ
Carroll
F I
FI
D000700:Analgesics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D001665:Binding Sites; D002352:Carrier Proteins; D003042:Cocaine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D003342:Corpus Striatum / Q000187:drug effects / Q000378:metabolism; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D011955:Receptors, Drug / Q000187:drug effects* / Q000378:metabolism; D013329:Structure-Activity Relationship
D000700:Analgesics; D002352:Carrier Proteins; D011955:Receptors, Drug; C061445:cocaine receptor; D003042:Cocaine