189949-97-1

Upstream product

• 140633-58-5 3β-(4-Chlorophenyl)-tropane-2β-carboxylic acid 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 130342-80-2 2β-carbomethoxy-3β-(4-chlorophenyl)tropane 
• 50373-10-9 methyl ecgonidine 

Downstream Products

• 140695-33-6 3β-(p-chlorophenyl)tropan-2β-carboxylic acid 2-(p-nitrophenyl)ethyl ester 
• 170939-91-0 3β-(4'-chlorophenyl)tropane-2β-N-phenacylcarboxamide 
• 189950-03-6 (1R,2S,3S,5S)-3-(4-Chloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid [2-(4-methoxy-benzylsulfanyl)-ethyl]-amide 
• 262423-84-7 2β-carbo-(S)-1'-mesyl-2-propoxy-3β-(4-chlorophenyl)tropane 
• 262423-82-5 2β-carbo-(R)-1'-mesyl-2-propoxy-3β-(4-chlorophenyl)tropane 

Relevant academic research and scientific papers

Synthesis and evaluation of novel tropane derivatives as potential PET imaging agents for the dopamine transporter

A novel series of tropane derivatives containing a fluorinated tertiary amino or amide at the 2β position was synthesized, labeled with the positron-emitter fluorine-18 (t1/2 = 109.8 min), and tested as potential in vivo dopamine transporter (D

Synthesis and evaluation of novel N-fluoropyridyl derivatives of tropane as potential PET imaging agents for the dopamine transporter

A series of novel N-fluoropyridyl-containing tropane derivatives were synthesized and their binding affinities for the dopamine transporter (DAT), serotonin transporter (SERT) and norepinephrine (NET) were determined via competitive radioligand binding as

Nicotinic acetylcholine receptor efficacy and pharmacological properties of 3-(substituted phenyl)-2β-substituted tropanes

There is a need for different and better aids to tobacco product use cessation. Useful smoking cessation aids, bupropion (2) and varenicline (3), share some chemical features with 3-phenyltropanes (4), which have promise in cocaine dependence therapy. Her

An extended study of dimeric phenyl tropanes

A series of dimeric phenyl tropanes consisting of two molecules of 4-chloro, 4-iodo or 4-(3-thiopheno)-phenyl tropane tethered together at the carboxylic acid moiety by a diamine or diol linker were prepared. The diamines used were a variety of linear, cyclic and aromatic diamines, while the diol tethered compounds were prepared by 'click' chemistry and contained a triazole in the linker. The new compounds were tested for binding to hDAT, hSERT and hNET. Amide linked chlorophenyl tropanes with an aromatic linker was found to be potent and selective DAT inhibitors with the best Ki value for hDAT being 6 nM. The ester linked halophenyl tropanes were more potent but displayed little selectivity in inhibition of monoamine transporter binding. Among the studied compounds an ester linker of 10 atoms between the tropane moieties gave the highest affinity. One monomeric phenyl tropane was made for comparison and was found to be less potent than the dimeric counterparts towards SERT and NET but remain highly active against DAT. Dimeric thiophenophenyl tropanes were in general found to be comparatively poor monoamine transporter binders, but significant gains of affinity of up to 45-fold could be achieved with selected dimeric chlorophenyl tropanes compared to the parent monomer. This observation implies that a secondary binding site that has affinity for phenyl tropanes, most likely the putative S2 site, is located within 13 A of the primary central S1 binding site.

Synthesis, monoamine transporter binding, properties, and functional monoamine uptake activity of 3β-[4-methylphenyl and 4-chlorophenyl]- 2β-[5-(substituted phenyl)thiazol-2-yl]tropanes

Synthetic methods were developed for the synthesis of the 3β-(4-substituted phenyl)-2β-[5-(substituted phenyl)thiazol-2-yl] tropanes (4a-s). The compounds were evaluated for their monoamine transporter binding and monoamine uptake inhibition properties using both rat brain tissue and cloned transporter assays. In general, the compounds showed higher dopamine transporter (DAT) affinity relative to the serotonin and norepinephrine transporters (SERT and NET, respectively) and greater [3H]dopamine uptake inhibition potency relative to [3H]serotonin and [ 3H]norepinephrine uptake inhibition. Several compounds were DAT selective relative to the SERT and NET in the monoamine transporter binding assays. The most potent and selective analog in the functional monoamine uptake inhibition test was 3β-(4-methylphenyl-2β-[5-(3-nitrophenyl)thiazol-2- yl]tropane (4p).

Synthesis and binding affinities of 2β-(3-iodoallyloxycarbonyl)-3β-(4-substituted-aryl)tropane analogues as ligands for the dopamine transporter studies

Tropane analogues from cocaine, which is known to be one of the most reinforcing and addictive compounds, were designed, synthesized, and characterized for inhibition of presynaptic uptake of dopamine (DA) in brain. Eight new derivatives of 3β-aryl-2β-(3-iodoallyloxycarbonyl)tropanes were synthesized and tested for their potential abilities to displace [3H]2β-carbomethoxy-3β-(4-fluorophenyl)tropane (WIN 35,428) binding to the rat striatal membranes.

Synthesis, biodistribution, and primate imaging of fluorine-18 labeled 2β-carbo-1'-fluoro-2-propoxy-3β-(4-chlorophenyl)tropanes. Ligands for the imaging of dopamine transporters by positron emission tomography

2β-(R)-Carbo-1-fluoro-2-propoxy-3β-(4-chlorophenyl)tropane ((R)-FIPCT, R-6) and 2β-(S)-carbo-1-fluoro-2-propoxy-3β-(4-chlorophenyl)tropane ((S)- FIPCT, S-6) were prepared and evaluated in vitro and in vivo for dopamine transporter (DAT) selectivity and sp

Synthesis and characterization of technetium-99m-labeled tropanes as dopamine transporter-imaging agents

In the development of novel Tc-99m-labeled tropane derivatives as dopamine transporter (reuptake site)-imaging agents, a series of neutral and lipophilic complexes containing bis-(aminoethanethiol) as a neutral complexing moiety for a [99mTc]Tc

Synthesis, ligand binding, and quantitative structure-activity relationship study of 3β-(4'-substituted phenyl)-2β-heterocyclic tropanes: Evidence for an electrostatic interaction at the 2β-position

A set of 3β-(4'-substituted phenyl)-2β-heterocyclic tropanes was designed, synthesized, and characterized. We discovered that these compounds can function as bioisosteric replacements for the corresponding WIN 35,065-2 analogs which possess a 2β-carbometh