TY - JOUR
T1 - Structure-activity relationship studies of highly selective inhibitors of the dopamine transporter
T2 - N-benzylpiperidine analogues of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl) piperazine
AU - Greiner, Elisabeth
AU - Prisinzano, Thomas
AU - Johnson, Edward M.
AU - Dersch, Christina M.
AU - Marcus, Jamila
AU - Partilla, John S.
AU - Rothman, Richard B.
AU - Jacobson, Arthur E.
AU - Rice, Kenner C.
PY - 2003/4/10
Y1 - 2003/4/10
N2 - A series of 4-[2-[bis(4-fluorophenyl)methoxy]ethyl-1-benzylpiperidines were examined for their ability to bind to the dopamine transporter (DAT), the serotonin transporter (SERT), and the norepinephrine transporter (NET). Binding results indicated that the presence of an electronwithdrawing group in the C4-position of the N-benzyl group is beneficial for binding to the DAT. Several analogues have been identified with high affinity for the DAT, up to 500-fold selectivity over the SERT and about 170-fold selectivity over the NET in binding and uptake inhibition assays.
AB - A series of 4-[2-[bis(4-fluorophenyl)methoxy]ethyl-1-benzylpiperidines were examined for their ability to bind to the dopamine transporter (DAT), the serotonin transporter (SERT), and the norepinephrine transporter (NET). Binding results indicated that the presence of an electronwithdrawing group in the C4-position of the N-benzyl group is beneficial for binding to the DAT. Several analogues have been identified with high affinity for the DAT, up to 500-fold selectivity over the SERT and about 170-fold selectivity over the NET in binding and uptake inhibition assays.
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U2 - 10.1021/jm020419v
DO - 10.1021/jm020419v
M3 - Article
C2 - 12672246
AN - SCOPUS:0037431420
SN - 0022-2623
VL - 46
SP - 1465
EP - 1469
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
IS - 8
ER -