13944-95-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(1,3-benzothiazol-2-ylsulfanyl)-1-phenylethanone is used as a building block for the synthesis of pharmaceuticals due to its unique chemical structure and properties. Its presence in various drug molecules contributes to their therapeutic effects and pharmacological activities.
Used in Agrochemical Industry:
In the agrochemical industry, 2-(1,3-benzothiazol-2-ylsulfanyl)-1-phenylethanone serves as a key intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds enhances their effectiveness in controlling pests and weeds, thereby improving crop yields and quality.
Used in Dye Industry:
2-(1,3-benzothiazol-2-ylsulfanyl)-1-phenylethanone is used as a precursor in the production of dyes, particularly those with specific color properties and stability. Its unique structure allows for the creation of dyes with desirable characteristics, making it an essential component in the dye industry.
Used in Organic Light-Emitting Diodes (OLEDs):
2-(1,3-benzothiazol-2-ylsulfanyl)-1-phenylethanone is used as a component in the development of organic light-emitting diodes due to its electronic and optical properties. Its incorporation into OLED materials contributes to improved device performance, such as enhanced brightness, efficiency, and stability.
Used as a Corrosion Inhibitor:
In the field of materials protection, 2-(1,3-benzothiazol-2-ylsulfanyl)-1-phenylethanone is used as a corrosion inhibitor. Its ability to form protective films on metal surfaces helps prevent corrosion and extends the service life of various metal components and structures.
Used in Antimicrobial Applications:
2-(1,3-benzothiazol-2-ylsulfanyl)-1-phenylethanone exhibits antimicrobial properties, making it a potential candidate for use in various applications, such as disinfectants, preservatives, and antimicrobial coatings. Its ability to inhibit the growth of microorganisms can contribute to improved hygiene and reduced risk of infection in various settings.
Used in Antioxidant Formulations:
Due to its antioxidant properties, 2-(1,3-benzothiazol-2-ylsulfanyl)-1-phenylethanone can be used in the development of antioxidant formulations for various industries, including food, cosmetics, and pharmaceuticals. Its ability to neutralize free radicals and prevent oxidative damage can help extend the shelf life of products and maintain their quality and safety.

Upstream product

• 532-27-4 1-chloroacetophenone 
• 2492-26-4 sodium 2-mercaptobenzothiazole 
• 149-30-4 2-Mercaptobenzothiazole 
• 70-11-1 α-bromoacetophenone 
• 23385-34-4 1-(benzothiazol-2-ylthio)propan-2-one 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 98-88-4 benzoyl chloride 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 98-86-2 acetophenone 
• 95-51-2 o-chloroaniline 
• 137-07-5 2-amino-benzenethiol 
• 7778-70-3 potassium 2-mercaptobenzothiazolate 
• 82248-73-5 2-(Benzothiazol-2-ylsulfanyl)-1-phenyl-2-phenylsulfanyl-ethanone 
• 120-78-5 di(benzothiazol-2-yl)disulfide 

Downstream Products

• 849-01-4 1,3,3-triphenylprop-2-en-1-one 
• 149-30-4 2-Mercaptobenzothiazole 
• 33415-92-8 1-phenyl-2-nonen-1-one 
• 5595-63-1 1-phenyl-2-hepten-1-one 
• 956-04-7 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 94-41-7 benzalacetophenone 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 2757-92-8 2-(ethylthio)benzothiazole 
• 3453-00-7 diethyl benzoylmethylphosphonate 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 98-86-2 acetophenone 
• 162707-85-9 2-(benzothiazol-2-thio)-1-phenyl-2-(2-propen-1-yl)-4-penten-1-one 
• 175600-63-2 2-(Benzothiazol-2-ylsulfanyl)-1-phenyl-pent-4-en-1-one 
• 175600-60-9 (E)-2-(Benzothiazol-2-ylsulfanyl)-1,5-diphenyl-pent-4-en-1-one 

Relevant academic research and scientific papers

A synthetic approach to tetrasubstituted alkenes: Using β-carbonyl benzothiazol-2-yl sulfones as electrophiles

A novel olefination method based on the modified Julia olefination reaction was developed. The reactions of β-carbonyl benzothiazol-2-yl sulfones with a series of alkynyllithiums and TMSCN gave the corresponding β-alkoxy sulfone intermediates, which under

Synthesis and monoamine oxidase A/B inhibitory evaluation of new benzothiazole-thiazolylhydrazine derivatives

In this study, a novel series of benzothiazole-thiazolylhydrazine (3a–3i) was synthesized and their structures were characterized by 1H-NMR, 13C-NMR spectrometry, and mass spectroscopy. These compounds were evaluated as inhibitors of

Developing a scaffold for urease inhibition based on benzothiazoles: Synthesis, docking analysis, and therapeutic potential

The synthesis, in silico molecular docking, and in vitro urease inhibition studies of a novel series of benzothiazole derivatives are reported. The title compounds in the two series, namely, 2-({5-[(benzothiazol-2-ylthio)methyl]-1,3,4-oxadiazol-2-yl}thio)-1-(4-substituted-phenyl)ethan-1-one and 2-(benzothiazol-2-ylthio)-1-(4-substituted-phenyl)ethan-1-one oxime, were synthesized by the reaction of benzo[d]thiazole-2-thiol with different kinds of intermediates in several steps using both conventional and microwave techniques. All compounds were found to have an excellent degree of urease-inhibitory potential ranging between 16.16 ± 0.54 and 105.32 ± 2.10 μM when compared with the standard inhibitor acetohydroxamic acid with IC50 = 320.70 ± 4.24 μM. The structure–activity relationship was established in detail. The binding interactions of the compounds with the enzyme were confirmed through molecular docking. Further, 100 -ns molecular dynamics simulations were performed to investigate the stability and structural perturbations experienced by the most potent compound over the urease active site.

High Chemo-/Stereoselectivity for Synthesis of Polysubstituted Monofluorinated Pyrimidyl Enol Ether Derivatives

A novel intramolecular Smiles rearrangement of α-fluoro-β-keto-pyrimidylsulfones (usually used as a carbon nucleophile) was developed, providing a versatile avenue for synthesis of tri/tetra-substituted monofluorinated pyrimidyl enol ethers. Among these, diverse (Z)-monofluorovinylsulfones and sulfinates were efficiently assembled by adding extra electrophile and fine-tuning reaction conditions. The process is triggered by a keto-enol tautomerism from enol oxyanion to pyrimidine 2-carbon, completely different from the classical carbon nucleophilic addition reaction approach.

CF2DSO2Na: An Effective Precursor Reagent for Deuteriodifluoromethylthiolation and Deuteriodifluoromethylation

Deuteriodifluoromethythio (SCF2D) and deuteriodifluoromethyl (CF2D) are important functional groups in pharmaceutical and agrochemical compounds, and the introduction of these functional groups remains a challenging. We herein report a robust reagent for deuteriodifluoromethylthiolation and deuteriodifluoromethylation. Its potentials were successfully showcased by deuteriodifluoromethylation and deuteriodifluoromethylthiolation of indoles with high-level deuterium incorporation. The reagent also has potential for deuteriodifluoromethylation and deuteriodifluoromethylthiolation of wide range of other natural or synthetic bioactive molecules.

Benzo[d]thiazole-2-thiol bearing 2-oxo-2-substituted-phenylethan-1-yl as potent selectivelasBquorum sensing inhibitors of Gram-negative bacteria

Quorum sensing is a well-known term for describing bacterial cell-cell communication. Bacteria use quorum sensing pathways to respond to external factors such as nutrient availability, defense mechanisms, and coordinate host toxic behaviors such as biofilm formation, virulence production, and other pathogenesis. Discovery of novel compounds which inhibit quorum sensing without being antibiotic are currently emerging fields. Herein, the library of fifteen benzo[d]thiazole/quinoline-2-thiol bearing 2-oxo-2-substituted-phenylethan-1-yl compounds was designed, synthesized and evaluated to find novel quorum sensing inhibitors. Firstly, compounds were evaluated for their growth inhibitory activities at high concentrations up to 1000 μg mL?1towardPseudomonas aeruginosa. Under our conditions, twelve compounds showed moderate growth inhibitory activities in the concentration tested. To our delight, three compounds3,6and7do not affect the growth of the bacteria which were chosen for the evaluation of quorum sensing inhibitor activities. In theLasBsystem, our compounds3,6,7showed promising quorum-sensing inhibitors with IC50of 115.2 μg mL?1, 182.2 μg mL?1and 45.5 μg mL?1, respectively. In thePqsRsystem, no activity observed suggesting that the selectivity of the compound toward theLasBsystem. In addition,7showed the moderate anti-biofilm formation ofPseudomonas aeruginosa. Docking studies revealed that3,6and7binding to the active site ofPseudomonas aeruginosaquorum sensingLasRsystem with better affinity compared to reference compounds4-NPO. Finally, computation calculations suggest that compounds are a good template for further drug development.

LEGO-Inspired Drug Design: Unveiling a Class of Benzo[d]thiazoles Containing a 3,4-Dihydroxyphenyl Moiety as Plasma Membrane H+-ATPase Inhibitors

The fungal plasma membrane H+-ATPase (Pma1p) is a potential target for the discovery of new antifungal agents. Surprisingly, no structure–activity relationship studies for small molecules targeting Pma1p have been reported. Herein, we disclose a LEGO-inspired fragment assembly strategy for the design, synthesis, and discovery of benzo[d]thiazoles containing a 3,4-dihydroxyphenyl moiety as potential Pma1p inhibitors. A series of 2-(benzo[d]thiazol-2-ylthio)-1-(3,4-dihydroxyphenyl)ethanones was found to inhibit Pma1p, with the most potent IC50 value of 8 μm in an in vitro plasma membrane H+-ATPase assay. These compounds were also found to strongly inhibit the action of proton pumping when Pma1p was reconstituted into liposomes. 1-(3,4-Dihydroxyphenyl)-2-((6-(trifluoromethyl)benzo[d]thiazol-2-yl)thio)ethan-1-one (compound 38) showed inhibitory activities on the growth of Candida albicans and Saccharomyces cerevisiae, which could be correlated and substantiated with the ability to inhibit Pma1p in vitro.

Zinc oxide catalyzed solvent-free mechanochemical route for C-S bond construction: A sustainable process

A zinc oxide catalyzed solvent-free mechanochemical process has been developed for the rapid construction of C-S bonds by using a nucleophilic substitution reaction (SN2 mechanism) that involves a variety of thiols and phenacyl/ benzyl/alkyl bromides. Notable advantages of this method in-clude its broad substrate scope, clean reaction profile, safety, scalability, high product yields at ambient conditions, and the recyclability of the catalyst. Furthermore, the prepared compounds are valuable building blocks for the synthesis of various biologically active molecules.

Esterase-sensitive sulfur dioxide prodrugs inspired by modified Julia olefination

Sulfur dioxide (SO2) is an endogenously produced gaseous molecule, and is emerging as a potential gasotransmitter. Herein, we describe the first series of esterase-sensitive prodrugs inspired by modified Julia olefination as SO2 donors.

Preparation method of alpha-heterocycle sulfide ketone compound

The invention provides a method for efficiently synthesizing different heterocycle sulfide ketone derivatives. According to the method, KI is adopted as a catalyst, potassium persulfate is adopted as an oxidizing agent, a carbonyl compound and benzoheterocycle mercaptan are taken as reaction substrates at room temperature, and DMSO is added into a reaction system as a solvent. The method provided by the invention has the advantages that the catalyst is cheap and available; reaction conditions are mild, and reaction can be carried out at room temperature, thereby being safe and reliable; and the highest yield of the obtained target product reaches 94%. The method provided by the invention overcomes the defects that a substrate of the traditional heterocycle thio etherification reaction is expensive, multi-step reaction is required to be carried out and reaction conditions are harsh, and the method provided by the invention has a good industrial application prospect.