94001-59-9

Upstream product

• 4237-48-3 diphenylmethanethiol 
• 107-07-3 2-chloro-ethanol 
• 108-86-1 bromobenzene 
• 100-52-7 benzaldehyde 
• 91-01-0 1,1-Diphenylmethanol 
• 60-24-2 2-hydroxyethanethiol 

Downstream Products

• 908583-36-8 benzhydryl(2-bromoethyl)sulfane 
• 908583-43-7 C₂₃H₂₉NO₂S 

Relevant academic research and scientific papers

Novel and High Affinity 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues as Atypical Dopamine Transporter Inhibitors

The development of pharmacotherapeutic treatments of psychostimulant abuse has remained a challenge, despite significant efforts made toward relevant mechanistic targets, such as the dopamine transporter (DAT). The atypical DAT inhibitors have received attention due to their promising pharmacological profiles in animal models of cocaine and methamphetamine abuse. Herein, we report a series of modafinil analogues that have an atypical DAT inhibitor profile. We extended SAR by chemically manipulating the oxidation states of the sulfoxide and the amide functional groups, halogenating the phenyl rings, and/or functionalizing the terminal nitrogen with substituted piperazines, resulting in several novel leads such as 11b, which demonstrated high DAT affinity (Ki = 2.5 nM) and selectivity without producing concomitant locomotor stimulation in mice, as compared to cocaine. These results are consistent with an atypical DAT inhibitor profile and suggest that 11b may be a potential lead for development as a psychostimulant abuse medication.

POTENT AND SELECTIVE INHIBITORS OF MONOAMINE TRANSPORTERS; METHOD OF MAKING; AND USE THEREOF

Disclosed herein are bisarylmethylthioacetamides and bisarylmethylthioethylamines useful as inhibitors of monoamine transporters. The compounds are potent and/or selective inhibitors of dopamine (DA), serotonin (5-HT), and/or norepinephrine (NE) reuptake via their respective transporters, DAT, SERT and NET. Also disclosed are methods for eliciting a wake-promoting or cognitive or attention enhancing effect and for treating substance use disorders, attention deficit (hyperactivity) disorder, depressive disorders, bipolar disorder or other neuropsychiatric disorders sleep disorders or cognitive impairment using the compounds.

Protic ionic liquids as recyclable solvents for the acid catalysed synthesis of diphenylmethyl thioethers

The acid catalysed formation of diphenylmethyl (DPM) thioethers was successfully achieved using the protic ionic liquid (pIL) triethylamine: methanesulfonic acid (TeaMs) as the reaction solvent under microwave irradiation. A slight excess of methanesulfon

Synthesis and biological evaluation of (R)-N-(diarylmethylthio/sulfinyl)ethyl/propyl-piperidine-3-carboxylic acid hydrochlorides as novel GABA uptake inhibitors

A series of new (R)-1-(2-diarylmethylthio/sulfinyl)ethyl-piperidine-3-carboxylic acid hydrochlorides 5a-d/6a-d and (R)-1-(3-diarylmethylthio)propyl-piperidine-3-carboxylic acid hydrochlorides 5′a-d were synthesized and evaluated as γ-aminobutyric acid uptake inhibitors through cultured cell lines expressing mouse GAT1. Biological screening results demonstrated that the compounds 6a-d with diarylmethylsulfinyl ethyl side chain show more potent GAT1 inhibitory activities than 5a-d/5′a-d with diarylmethylthio ethyl/propyl moieties. Some of them, such as 6a, exhibited excellent inhibitions of [3H]-GABA uptake in cultured cells, which is 496-fold higher than (R)-nipecotic acid and 11.5 times less than tiagabine. The synthesis and structure-activity relationships are discussed.

An efficient and chemoselective method for protection of thiols catalyzed by aluminumdodecatungstophosphate (AlPW12O40), as a highly water tolerant Lewis acid catalyst

Protection of various thiols with diphenylmethanol was achieved in high yields at room temperature using catalytic amounts of AlPW12O 40 in CH2Cl2. In the presence of this catalyst, protection of SH versus OH was achieved with high chemoselectivity and yields. The catalyst can be easily recovered and reused. Deprotection of DPM thioethers was also achieved using molecular iodine at reflux in CH2Cl 2 in high yields.

Various N-substituted 3-piperidine carboxylic acids or N-substituted 3-pyridinecarboxylic acids and derivatives thereof

Analogs of nipecotic acid are the novel compounds of the present invention. The analogs are GABA uptake inhibitors for use to treat epilepsy and, thus, the invention is also pharmaceutical compositions and methods of use therefor.