79295-14-0

Upstream product

• 696-63-9 4-Methoxybenzenethiol 
• 96-34-4 methyl chloroacetate 
• 2365-48-2 Methyl thioglycolate 
• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 
• 96-32-2 bromoacetic acid methyl ester 
• 3517-99-5 1-methoxy-4-(methylsulfinyl)benzene 
• 67-56-1 methanol 
• 108127-50-0 ethynyl(4-methoxyphenyl)sulfane 
• 109047-48-5 1,2-Dichlor-1-<4-methoxy-phenylmercapto>-aethylen 
• 3406-77-7 (4-methoxy-phenylsulfanyl)-acetic acid 

Downstream Products

• 125706-38-9 (+/-)-Methyl <(4-methoxyphenyl)sulfinyl>acetate 
• 3406-77-7 (4-methoxy-phenylsulfanyl)-acetic acid 

Relevant academic research and scientific papers

Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2

An efficient electrochemical synthesis approach of various unsymmetrical thioethers and arylboronates has been developed. Bench stable arylazo sulfones were used as radical precursors for carbon-heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and even added bases, but also exhibited favorable functional group tolerance. (Figure presented.).

Sulfoxide Reduction/C(sp3)-S Metathesis Cascade in Ionic Liquid

A sulfoxide reduction/C-S bond metathesis cascade between sulfoxides and alkyl bromides has been developed to access high-value sulfides without the use of any catalysts or bases. In this cascade, classical Kornblum oxidation is employed to reduce sulfoxides with alkyl bromides in ionic liquid. This protocol features high functional tolerance, mild conditions, promising scalability, and sustainable solvents.

Gold-Catalyzed Oxidation of Thioalkynes to Form Phenylthio Ketene Derivatives via a Noncarbene Route

Gold-catalyzed oxidations of thioalkynes with 8-methylquinoline oxides afford 2-phenylthioketenes that can be trapped efficiently with alcohols. The synthetic utility is manifested by terminal and internal thioalkynes over a wide scope, bearing esters, ke

Design, synthesis, and biological evaluation of novel pan agonists of FFA1, PPARγ and PPARδ

The free fatty acid receptor 1 (FFA1) and peroxisome proliferator-activated receptors (PPARs) have attracted interest as potent targets for the treatment of metabolic syndrome such as type 2 diabetes. Based on the hypothesis that the dual agonists of PPARs and FFA1 would act as insulin sensitizers and secretagogues by simultaneous activation of PPARs and FFA1, we developed the design strategy to obtain dual PPARs/FFA1 agonist by hybrid FFA1 agonist 1 with PPARδ agonist 2 in consideration of their structural similarity. As expected, systematic exploration of structure-activity relationship and molecular modeling, results in the discovery of lead compound 15, a pan agonist with relative balanced activities between FFA1, PPARγ and PPARδ. The dose-response relationship studies suggested that the pan agonist 15 suppressed the excursion of blood glucose levels in a dose-dependent manner. During a 5-days treatment in ob/ob mice, the pan agonist 15 (100 mg/kg) revealed sustained hypoglycemic effect, even proximity to the most advanced FFA1 agonist (TAK-875, 40 mg/kg), which might be attributed to its pan PPARs/FFA1 activities to simultaneous regulate the mechanism of insulin secretion and resistance. These positive results suggest that the dual PPARs/FFA1 agonists such as lead compound 15 might be novel therapeutic strategy to modulate the complex pathological mechanisms of type 2 diabetes.

Discovery of phenylsulfonyl acetic acid derivatives with improved efficacy and safety as potent free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1) has emerged as an attractive anti-diabetic target that mediates glucose-stimulated insulin secretion. Several FFA1 agonists have been reported, but many of them possessed somewhat high lipophilicity and/or molecular weight. Herein, we describe the identification of sulfone-carboxylic acid moiety with the multiple advantages of reducing lipophilicity, cytotoxicity and β-oxidation associated with compound 2. Further structure-activity relationship study based on the previleged scaffolds led to the discovery of 2-{(4-[(2’-chloro-[1,1’-biphenyl]-3-yl)methoxy]phenyl)sulfonyl}acetic acid (compound 20), which showed a better balance than compound 2 in terms of physicochemical properties, cytotoxicity profiles and pharmacokinetic properties. Subsequent in vivo studies demonstrated that compound 20 robustly improves the glucose tolerance both in normal and type 2 diabetic models without the risk of hypoglycemia. Compared to the high risk of TAK-875 induced liver toxicity, there was no significant adverse effects such as hepatic and renal toxicity were observed in the chronic toxicity studies of compound 20 even at the higher dose.

Facile synthetic approaches to 1-thiocyclopropanecarboxylates

Two facile synthetic approaches to the novel biologically interesting 1-thiocyclopropanecarboxylates starting from corresponding thiols were developed. Approach A involved five steps with the key steps being the SN2 reactions of thiols and α-br

Catalyst-free photoredox addition-cyclisations: Exploitation of natural synergy between aryl acetic acids and maleimide

Suitably functionalised carboxylic acids undergo a previously unknown photoredox reaction when irradiated with UVA in the presence of maleimide. Maleimide was found to synergistically act as a radical generating photoxidant and as a radical acceptor, negating the need for an extrinsic photoredox catalyst. Modest to excellent yields of the product chromenopyrroledione, thiochromenopyrroledione and pyrroloquinolinedione derivatives were obtained in thirteen preparative photolyses. In situ NMR spectroscopy was used to study each reaction. Reactant decay and product build-up were monitored, enabling reaction profiles to be plotted. A plausible mechanism, whereby photo-excited maleimide acts as an oxidant to generate a radical ion pair, has been postulated and is supported by UV/Vis. spectroscopy and DFT computations. The radical-cation reactive intermediates were also characterised in solution by EPR spectroscopy. UVA photolyses of aryloxy-, arylthio- and arylamino-acetic acids with maleimide yield oxa-, thia- and aza-tricyclo pyrroledione derivatives in the absence of a photoredox catalyst (see scheme). An intriguing mechanism has been proposed and has been supported and supplemented by NMR monitoring experiments, DFT computations and UV/Vis and EPR spectroscopy.

Pyrolysis of (2-Phenylethyl)phenylsulfonium Ylides

In order to obtain information concerning the reaction mechanism of the pyrolysis of sulfonium ylides bearing a substituted phenyl group on the 2-position in the S-ethyl group of ethylphenylsulfonium ylide, (2-phenylethyl)phenylsulfonium bis(methoxycarbonyl)methylide (1) and dicyanomethylide(2) were subjected to pyrolysis in benzene.The reaction rates of 1 and 2 at 140 deg C were 6.0- and 3.2-times faster than those of ethylphenylsulfonium bis(methoxycarbonyl)methylide and dicyanomethylide, respectively.The activation parameters for 1 were ΔH++=125 kJ mol-1 and ΔS++=-3.8 JK-18mol-1, while those for 2 were ΔH++=124 kJ mol-1 and ΔS++=-2.5 JK-1 mol-1.Substituent efects on the β-phenyl groups in 1 and 2 afforded positive Hammett ρ-values: ρ = 0.49 (γ = 0.997) and ρ = 0.26 (γ = 0.993), respectively.From the obtained results, it was suggested that the pyrolysis proceeds through essentially a concerted intramolecular cis-elimination inclined toward a slightly carbanion-like type from an E1-like type by introducing a phenyl substituent at the 2-position of the ethyl group in the ethylphenylsulfonium ylide.

A FACILE ROUTE TO HOMOCHIRAL SULFOXIDES

Biocatalytic resolution of methyl sulfinylacetates afford sulfoxides (R)-(1)-(6) in very high optical yields; the products have been used in a systematic study of the "SPAC" reaction, an asymmetric synthesis of γ-hydroxy-α,β-unsaturated esters.

Applicability of Hammett Equation to Kinetics of Acid-catalysed Esterification of meta- and para-Substituted Phenylmercaptoacetic and Phenylsulphonylacetic Acids with Methanol

Rate constants have been determined for the acid-catalysed esterification of meta- and para-substituted phenylmercaptoacetic and phenylsulphonylacetic acids with methanol using hydrogen chloride as catalyst.The lower reactivities of phenylmercaptoacetic acids compared to those of the corresponding phenoxyacetic acids are discussed.