66086-38-2

Upstream product

• 700-96-9 3,4-dimethoxythiophenol 
• 91-16-7 1,2-dimethoxybenzene 
• 1357595-53-9 3,4-dimethoxyphenyl triphenylmethyl sulfide 
• 23095-31-0 3,4-dimethoxybenzene-1-sulfonyl chloride 

Downstream Products

• 116424-06-7 1,4-dimethoxy-2,5-bis(3,4-dimethoxyphenylthio)benzene 
• 70339-47-8 1,2-Bis-(3,4-dimethoxy-phenylsulfanyl)-4,5-dimethoxy-benzene 
• 198421-57-7 3S-(3,4-dimethoxyphenylthio)-2S-isobutylbutan-1,4-dioic acid 4-tert-butyl ester 
• 198421-59-9 N²-[4-tert-butyloxy-3S-(3,4-dimethoxyphenylthio)-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide 
• 198421-56-6 N²-[3S-(3,4-dimethoxyphenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide 

Relevant academic research and scientific papers

A green disulfide synthesis method

The present invention discloses a green disulfide synthesis method, belonging to the field of green chemical and organic synthesis technology. Under room temperature, open, neutral conditions, rapid preparation of parent nuclei is alkanes, olefins, aromatic hydrocarbons, oxazole, thiazole, pyrazole, imidazole, etc. and their derivatives of symmetrical disulfide, the catalyst is MBrx(M is Fe2+,Fe3+,Ce3+, etc., x is 2-3), the only oxidant isH2O2. The present invention is reacted by using commercially available and low-cost reagents (e.g., FeBr2,CeBr3 andH2O2,etc.) and common organic solvents, the steps are concise, the operation is convenient, the reaction is rapid, the reaction conditions are mild, the room temperature is open, and no further purification can be obtained pure disulfide, more advantageous than all previous methods, is expected to be in organic synthesis, medicine, Pesticides and electronics and other industries are widely used.

Visible-light photocatalytic selective aerobic oxidation of thiols to disulfides on anatase TiO2

This work presents the visible-light photocatalytic selective oxidation of thiols to disulfides with molecular oxygen (O2) on anatase TiO2. The high specific surface area of anatase TiO2 proved to be especially critical in

TEMPO visible light photocatalysis: The selective aerobic oxidation of thiols to disulfides

TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) is well-established in orangocatalysis that usually work in synergy with transition-metal catalysis or semiconductor photocatalysis. Here, TEMPO was turned into a visible light photocatalyst to conduct the selective aerobic oxidation of thiols into disulfides. With O2 as an oxidant, a mild and efficient protocol for the selective oxidation of thiols into disulfides including symmetrical and unsymmetrical ones with 5 molpercent of TEPMO as a photocatalyst was developed at room temperature under the irradiation of 460 nm blue LEDs. It was found that a complex formed between TEMPO and thiols underpinned the visible light activity and disulfides were obtained in very high isolated yields. This work suggests that TEMPO takes diverse roles in for photocatalytic selective oxidative transformations with O2 as the oxidant.

Biocatalytic synthesis of diaryl disulphides and their bio-evaluation as potent inhibitors of drug-resistant Staphylococcus aureus

Staphylococcus aureus is a WHO Priority II pathogen for its capability to cause acute to chronic infections and to resist antibiotics, thus severely impacting healthcare systems worldwide. In this context, it is urgently desired to discover novel molecules to thwart the continuing emergence of antimicrobial resistance. Disulphide containing small molecules has gained prominence as antibacterials. As their conventional synthesis requires tedious synthetic procedure and sometimes toxic reagents, a green and environmentally benign protocol for their synthesis has been developed through which a series of molecules were obtained and evaluated for antibacterial activity against ESKAPE pathogen panel. The hit compound was tested for cytotoxicity against Vero cells to determine its selectivity index and time-kill kinetics was determined. The activity of hit was determined against a panel of S. aureus multi-drug resistant clinical isolates. Also, its ability to synergize with FDA approved drugs was tested as was its ability to reduce biofilm. We identified bis(2-bromophenyl) disulphide (2t) as possessing equipotent antimicrobial activity against S. aureus including MRSA and VRSA strains. Further, 2t exhibited a selectivity index of 25 with concentration-dependent bactericidal activity, synergized with all drugs tested and significantly reduced preformed biofilm. Taken together, 2t exhibits all properties to be positioned as novel scaffold for anti-staphylococcal therapy.

ANTI-BACTERIAL COMPOUNDS

A compound of Formula (II): for use in the prevention or treatment of a bacterial infection.

Bovine serum albumin triggered waste-free aerobic oxidative coupling of thiols into disulphides on water: An extended synthesis of bioactive dithiobis(phenylene)bis(benzylideneimine) via sequential oxidative coupling-condensation reactions in one pot from aminothiophenol and benzaldehyde

Bovine serum albumin (BSA) has been explored for aerobic oxidative coupling of thiols (aromatic, heterocyclic as well as aliphatic) "on water" towards formation of disulphides (SS) without using any metal/non-metal complexes, bases and additives, which renders the process environmentally benign and economically attractive with good recyclability (up to four cycles). The developed green protocol was further extended for synthesis of diallyldisulphide (DADS), an important constituent of natural occurring allicin. Among various synthesized disulphides, bis(2-aminophenyl)disulphide, obtained by oxidative coupling of 2-aminothiophenol in BSA, was further utilized for condensation with benzaldehyde in the same pot thus enabling easy access to bioactive dithiobis(phenylene)bis(benzyldeneimine). This is the first example of BSA catalysed sequential (oxidation/condensation) reaction where one SS and two CN bonds are formed solely "on water."

C-S bond cleavage in aromatic sulfide radical cations

The results of our recent studies of the structural effects on the C-S bond fragmentation process of aromatic sulfur radical cations are reported.

Enzymatic- and iridium-catalyzed asymmetric synthesis of a benzothiazepinylphosphonate bile acid transporter inhibitor

A synthesis of the benzothiazepine phosphonic acid 3, employing both enzymatic and transition metal catalysis, is described. The quaternary chiral center of 3 was obtained by resolution of ethyl (2-ethyl)norleucinate (4) with porcine liver esterase (PLE) immobilized on Sepabeads. The resulting (R)-amino acid (5) was converted in two steps to aminosulfate 7, which was used for construction of the benzothiazepine ring. Benzophenone 15, prepared in four steps from trimethylhydroquinone 11, enabled sequential incorporation of phosphorus (Arbuzov chemistry) and sulfur (Pd(0)-catalyzed thiol coupling) leading to mercaptan intermediate 18. S-Alkylation of 18 with aminosulfate 7 followed by cyclodehydration afforded dihydrobenzothiazepine 20. Iridium-catalyzed asymmetric hydrogenation of 20 with the complex of [Ir(COD)2BArF] (26) and Taniaphos ligand P afforded the (3R,5R)-tetrahydrobenzothiazepine 30 following flash chromatography. Oxidation of 30 to sulfone 31 and phosphonate hydrolysis completed the synthesis of 3 in 12 steps and 13% overall yield.

Structural and solvent effects on the C-S bond cleavage in aryl triphenylmethyl sulfide radical cations

Steady-state and laser flash photolysis (LFP) studies of a series of aryl triphenylmethyl sulfides [1, 3,4-(CH3O)2-C 6H3SC(C6H5)3; 2, 4-CH3O-C6H4SC(C6H5) 3; 3, 4-CH3-C6H4SC(C 6H5)3; 4, C6H5SC(C 6H5)3; and 5, 4-Br-C6H 4SC(C6H5)3] has been carried out in the presence of N-methoxyphenanthridinium hexafluorophosphate in CH 3CN, CH2Cl2, CH2Cl 2/CH3CN, and CH2Cl2/CH3OH mixtures. Products deriving from the C-S bond cleavage in the radical cations 1?+-5?+ have been observed in the steady-state photolysis experiments. Time-resolved LFP showed first-order decay of the radical cations accompanied by formation of the triphenylmethyl cation. A significant decrease of the C-S bond cleavage rate constants was observed by increasing the electron-donating power of the arylsulfenyl substituent, that is, by increasing the stability of the radical cations. DFT calculations showed that, in 2?+ and 3?+, charge and spin densities are mainly localized in the ArS group. In the TS of the C-S bond cleavage an increase of the positive charge in the trityl moiety and of the spin density on the ArS group is observed. The higher delocalization of the charge in the TS as compared to the initial state is probably at the origin of the observation that the C-S bond cleavage rates decrease by increasing the polarity of the solvent.

Tricyclic fused heterocycle compounds, process for preparing the same and use thereof

Compounds represented by formula (1), wherein X is, for example, CH, CH2, CHR (wherein R is a lower alkyl group or a substituted lower alkyl group) or CRR′ (wherein R and R′ are the same as the above defined R); Y is, for example, CH, CH2or C═O; Z is, for example, O, S, S=O or SO2; U is C or N; R1to R4are each independently, for example, a hydrogen atom, OR, SR (wherein R is the same as defined above), or an aromatic ring, a substituted aromatic ring or a heterocycle; at least one of R5and R8is, for example, OH and the remaining of R5and R8are each independently, for example, a hydrogen atom or OH, optical isomers thereof, conjugates thereof or pharmaceutically acceptable salts thereof are provided. These compounds are characterized in having a wide range of pharmacological actions such as an excellent relaxing action of tracheal smooth muscles, an inhibition of airway hypersensitivity and an inhibition of infiltration of inflammatory cells into the airway and, in addition, high safety.