615-22-5

Usage

Uses

Used in Water Treatment Industry:
2-Methylmercaptobenzothiazole is used as a pollutant remover for enhancing the quality of drinking water. Its chemical structure allows it to interact with and eliminate contaminants, ensuring a safer and cleaner water supply.
Used in Environmental Analysis:
2-Methylmercaptobenzothiazole serves as a reagent in the trace determination of polar 1H-benzotriazoles and benzothiazoles in drinking and surface water. It plays a crucial role in liquid chromatography-electrospray mass spectrometry techniques, enabling accurate and sensitive detection of these compounds for environmental monitoring and protection.

Metabolic pathway

When 2-methylthiobenzothiazole and 35S-labeled glutathione (GSH) are incubated with rat liver microsomes, both 35S-labeled S-(2- benzothiazolyl)glutathione and 2- mercaptobenzothiazole are isolated from the reaction mixtures. Glutathione-S-transferase appears to be involved in the S-(2- benzothiazolyl)glutathione formation. Although sulfur is exchanged in this pathway, the net result of this pathway which involves oxidation of the methylthio group and GSH conjugation is an apparent S-demethylation of the methylthio group. Another S-demethylation pathway that does not involve GSH conjugation also functions in vitro.

InChI:InChI=1/C8H7NS2/c1-5-9-8-6(10)3-2-4-7(8)11-5/h2-4,10H,1H3

Upstream product

• 67-56-1 methanol 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 2254-94-6 3-methylbenzothiazole-2-thione 
• 6011-99-0 benzo[d]thiazol-2-yl thiocyanate 
• 74-83-9 methyl bromide 
• 149-30-4 2-Mercaptobenzothiazole 
• 63451-39-8 S-benzothiazol-2-yl-N,N-dibutyl-thiohydroxylamine 
• 96-36-6 methyl phosphite 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 2801-21-0 benzothiazole sulfenamide 

Downstream Products

• 16768-72-2 1-methyl-2-(3-methyl-3H-benzothiazol-2-ylidenemethyl)-quinolinium; iodide 
• 15941-82-9 (3-ethyl-benzothiazol-2-yl)-(1-ethyl-[4]quinolyl)-methinium ; iodide 
• 101317-85-5 bis-(3-methyl-benzothiazol-2-yl)-azamethinium ; toluene-4-sulfonate 
• 112577-41-0 (3-methyl-benzothiazol-2-yl)-(2-methyl-6-phenyl-pyridazin-3-yl)-methinium ; bromide 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 2254-94-6 3-methylbenzothiazole-2-thione 
• 60372-32-9 2-(cyclohexylthio)benzo[d]thiazole 
• 202002-02-6 3-cyclohexylbenzo[d]thiazole-2(3H)-thione 
• 106061-12-5 5-[2-(3-methyl-3H-benzothiazol-2-ylidene)-ethylidene]-3-phenyl-2-thioxo-thiazolidin-4-one 
• 33682-61-0 3-benzylbenzo[d]thiazole-2(3H)-thione 
• 41614-08-8 3-ethyl-2-methylsulfanyl-benzothiazolium; iodide 
• 87515-67-1 2-ethylthio-3-ethylbenzothiazolinium iodide 
• 20064-98-6 2-methylthio-3-methylbenzothiazolium iodide 
• 112657-15-5 2-ethylsulfanyl-3-methyl-benzothiazolium; iodide 

Relevant academic research and scientific papers

New derivatives of 2-mercaptobenzotellurazole

New derivatives of 2-mercaptobenzotellurazole at the three reaction centers, the thiol group, nitrogen atom and tellurium atom, have been synthesized.

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

Selective and mild sulfoxidation of 2-sulfylbenzothiazole using hydroperoxides derived from cyclohexanone in the absence of catalyst

Alkyl hydroperoxides derived from cyclohexanone are attractive oxidants because they are easily available, more reactive than TBHP but much less acidic than m-CPBA. Wherein 1,1′-peroxybis(1-hydroperoxycyclohexane) (C) can be generated by the current simply method and displays the excellent reactivity and selectivity based on oxidative reactions of various benzothiazolyl sulfides substituted by different function groups. The research found that the reactions can be performed in the absence of catalyst and under very mild conditions optimized. Yields of sulfoxides is higher than 90%, no or a little reaction happened at the proximal double bond、 N and S atoms in the benzothiazolyl moiety. Phenyl sulfide as the substrates was also examined for the reaction scope test. The results show that they were uniquely and completely oxidized to sulfoxides in 1 h. A mild, environmentally friendly, catalyst-free aryl sulfide sulfoxidation method has been developed.

RNA-targeting low-molecular-weight fluorophores for nucleoli staining: synthesis,in silicomodelling and cellular imaging

Herein we present our work on the synthesis, investigation of the photophysical properties, interactions with nucleic acids, molecular docking, and imaging application of three carbocyanine dyes. The described low-molecular-weight compounds were found to exhibit high resistance against photobleaching and showed promising optical properties as fluorescent labeling agents for ribonucleic acids. They form strong biocomplexes (log?Ks= 6.11-7.84) and revealed remarkable sensitivity towards RNA, reaching up to a 379 times increase of the emission signal when bound to AU-rich sequences. According to the score values obtained from the molecular docking studies, the compounds show strong binding affinity towards RNA macromolecules. All fluorophores exhibit significant cell tolerance since they were found to be 16 to 60 times less toxic against MRC5 cells (healthy human fibroblasts) compared to the conventional Thiazole Orange - TO. The IC50 concentrations for the compounds were calculated up to 40 μM in human fibroblasts MRC5, A549 adenocarcinomic human alveolar basal epithelial cells, the HCT116 human colon cancer cell line, and MDA-MB-231 adenocarcinoma cells. Analyzing the dyes for preferential cytotoxicity towards cancer cell lines in comparison to the normal human fibroblasts, we found a candidate exhibiting promising anticancer potential. Based on the selectivity (Si) towards cancer cells and more specifically against difficult to treat colon HCT116 carcinoma, we can suggest these small molecules as an interesting platform for further development. We have also demonstrated the efficiency of the carbocyanines as staining agents forin vivolabeling of human cells as well as microbial and eukaryotic cells.

Inhibitors of heat shock protein 70 (Hsp70) with enhanced metabolic stability reduce tau levels

The molecular chaperone, Heat Shock Protein 70 (Hsp70), is an emerging drug target for neurodegenerative diseases, because of its ability to promote degradation of microtubule-associated protein tau (MAPT/tau). Recently, we reported YM-08 as a brain penetrant, allosteric Hsp70 inhibitor, which reduces tau levels. However, the benzothiazole moiety of YM-08 is vulnerable to metabolism by CYP3A4, limiting its further application as a chemical probe. In this manuscript, we designed and synthesized seventeen YM-08 derivatives by systematically introducing halogen atoms to the benzothiazole ring and shifting the position of the heteroatom in a distal pyridine. In microsome assays, we found that compound JG-23 has 12-fold better metabolic stability and it retained the ability to reduce tau levels in two cell-based models. These chemical probes of Hsp70 are expected to be useful tools for studying tau homeostasis.

Ag-Cu copromoted direct C2-H bond thiolation of azoles with Bunte salts as sulfur sources

A direct C2-H thiolation of azoles with Bunte salts was achieved under the combined action of copper and silver salts. This protocol could furnish various substituted 2-thioazoles in moderate to good yields. This method has a broad substrate scope and shows good functional group tolerance.

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)2(dtbbpy)]PF6 or fac-Ir(ppy)3 is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching mechanisms, offering complementary reactivity. The mild nature of the radical deoxygenation process enables the reduction of a wide range of functionalized sulfoxides, including those containing acid-sensitive groups, in typically high isolated yields.

Palladium-catalyzed intermolecular transthioetherification of aryl halides with thioethers and thioesters

Functional group transfer reactions are an important synthetic tool in modern organic synthesis. Herein, we developed a new palladium-catalyzed intermolecular transthioetherification reaction of aryl halides with thioethers and thioesters. The synthetic utility and practicality of this catalytic protocol are demonstrated in a wide range of successful transformations (>70 examples). This catalytic protocol is applicable in carbonylative coupling processes as well, and the first example of carbonylative methylthioesterification of aryl halides has been achieved. Notably, this work also provides an approach to using natural products, such as methionine and selenomethionine, as the functional group sources.

Thiazole orange – Spermine conjugate: A potent human telomerase inhibitor comparable to BRACO-19

In this report, we synthesized a series of TO conjugates containing different amino side chains and investigated their binding to telomeric G-quadruplex DNA (G4) using several biophysical methods including fluorometric titration and thermal denaturation monitored by fluorescence and circular dichroism. The composition of side chains strongly affects the binding of these molecules to G-quadruplex DNA. Incorporation of amino side chains increases the binding affinity of TO toward G4 but has a minimal effect on its selectivity for G4 over duplex DNA. The plausible binding modes are a synergistic effect of end-stacking and groove interactions as indicated by docking studies. Inhibition of human telomerase activity by TO derivatives was determined in vitro by the TRAP assay. Several derivatives can selectively inhibit the activity of telomerase over DNA polymerase at low concentrations. More significantly, TO-spermine conjugate (16) exhibits a remarkable effect on telomerase inhibition in the submicromolar range, which is comparable to the inhibition effect of a well-known G4 ligand, BRACO-19. Our results here provide guidance of utilizing TO derivatives as a viable scaffold to design novel G4 ligands, G4 probes, and potent telomerase inhibitors.

BF3·SMe2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles

Herein, a general, solvent-free and straightforward thiomethylation of electron deficient heterocycles using BF3·SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3·SMe2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non-malodorous reagent while the discovery of novel chemical transformations using BF3·SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent.