143966-02-3Relevant academic research and scientific papers
Synthesis and monoamine transporter affinity of 3′-analogs of 2-β-carbomethoxy-3-β-(4′-iodophenyl)tropane (β-CIT)
Bois, Frederic,Baldwin, Ronald M.,Kula, Nora S.,Baldessarini, Ross J.,Innis, Robert B.,Tamagnan, Gilles
, p. 2117 - 2120 (2007/10/03)
The 3′-iodo positional isomer of 2-β-carbomethoxy-3-β- (4′-iodophenyl)tropane (β-CIT) and other 3′-substituted analogs were synthesized and evaluated for binding to monoamine transporters in rat forebrain and membranes of cell lines selectively expressing human transporter genes. All 3′-substituted compounds displayed affinity for both serotonin (SERT) and dopamine (DAT), but much less for norepinephrine transporters (NET), with selectivity for rat (r) or human (h) SERT over NET, but only 3′-iodo-substituted phenyltropanes showed selectivity for SERT versus DAT. The 3′-iodo, N-methyl analog of β-CIT (7) displayed 29-fold selectivity and high affinity for hSERT (Ki=9.6nM) over hDAT (K i=279nM), and its nor-congener (8) showed even higher hSERT potency (Ki=1.2nM) and selectivity over DAT (415-fold).
Synthesis, Ligand Binding, and QSAR (CoMFA and Classical) Study of 3β-(3'-Substituted phenyl)-, 3β-(4'-substituted phenyl)-, and 3β-(3',4'-Disubstituted phenyl)tropane-2β-carboxylic Acids Methyl Esters
Carroll, F. Ivy,Mascarella, S. Wayne,Kuzemko, Michael A.,Gao, Yigong,Abraham, Philip,et al.
, p. 2865 - 2873 (2007/10/02)
Several new 3β-(4'-substituted phenyl), 3β-(3'-substituted phenyl), and 3β-(3',4'-disubstituted phenyl)tropane-2β-carboxylic acid methyl esters were prepared and assayed for inhibition of 3H>WIN 35,428 binding to the dopamine transporter.The 3
Substituted 3-Phenyltropane Analogs of Cocaine: Synthesis, Inhibition of Binding at Cocaine Recognition Sites, and Positron Emission Tomography Imaging
Meltzer, P. C.,Liang, A. Y.,Brownell, A.-L.,Elmaleh, D. R.,Madras, B. K.
, p. 855 - 862 (2007/10/02)
It is now accepted that (-)-cocaine binds to specific recognition sites associated with monoamine transporters in the mammalian brain. In this study, several analogs of 3β-phenyltropane-2β-carboxylic acid methyl ester were prepared and their potency for inhibiting the binding of -3β-(4-fluorophenyl)tropane-2β-carboxylic acid methyl ester to primate caudate-putamen was evaluated. The synthesis and binding affinity of 3β-(3,4-dichlorophenyl)tropane-2β-carboxylic acid methyl ester, one of the most potent cocaine congeners yet reported, is presented. The feasibility of synthesizing high-affinity ligands for cocaine recognition sites and their suitability as PET imaging ligands for cocaine receptors in vivo is demonstrated.
