7442-07-1

Usage

Uses

Used in the Rubber Industry:
6-Amino-2-Mercaptobenzothiazole is utilized as a vulcanization accelerator in the rubber industry. Its amino and mercapto functional groups contribute to the enhancement of the vulcanization process, improving the rubber's physical properties such as tensile strength, elasticity, and resistance to wear.
Used as an Intermediate in Chemical Synthesis:
In the realm of chemical synthesis, 6-Amino-2-Mercaptobenzothiazole serves as a versatile intermediate. Its functional groups can be further reacted or modified to produce a variety of derivative compounds for use in different applications, including pharmaceuticals, dyes, and other specialty chemicals.

InChI:InChI=1/C7H6N2S2/c8-4-1-2-5-6(3-4)11-7(10)9-5/h1-3H,8H2,(H,9,10)

Upstream product

• 75-15-0 carbon disulfide 
• 507246-12-0 2,5-diaminothiophenol 
• 2407-11-6 2-chloro-6-nitrobenzothiazole 
• 64-17-5 ethanol 
• 137-07-5 2-amino-benzenethiol 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 4845-58-3 6-nitrobenzo[d]thiazole-2(3H)-thione 
• 149-30-4 2-Mercaptobenzothiazole 
• 4845-58-3 2-mercapto-6-nitrobenzothiazole 
• 14791-78-7 2-fluoro-para-phenylenediamine 
• 140-92-1 potassium isopropylxanthate 
• 140-89-6 potassium ethyl xanthogenate 
• 540-24-9 p-phenylenediamine hydrochloride 

Downstream Products

• 71085-90-0 N,N'-bis-(2-thioxo-2,3-dihydro-benzothiazol-6-yl)-urea 
• 121690-17-3 (2-thioxo-2,3-dihydro-benzothiazol-6-yl)-urea 
• 7340-70-7 N-(2-thioxo-2,3-dihydrobenzo[d]thiazol-6-yl)acetamide 
• 16946-14-8 N-(2-thioxo-2,3-dihydrobenzo[d]thiazol-6-yl)benzamide 
• 25801-92-7 6-Amino-2-hydroxycarbonylmethylmercapto-benzthiazol 
• 54420-94-9 6-iodo-3H-benzothiazole-2-thione 
• 884238-41-9 C₁₆H₁₅N₃OS₂ 
• 901116-32-3 C₁₆H₁₄FN₃OS₂ 
• 532422-39-2 C₁₇H₁₇N₃O₂S₂ 
• 530137-01-0 C₁₇H₁₇N₃OS₂ 
• 318258-80-9 C₁₅H₁₃N₃OS₂ 
• 358626-40-1 C₁₅H₁₂ClN₃OS₂ 
• 303063-09-4 C₁₅H₁₂FN₃OS₂ 
• 341952-66-7 C₁₆H₁₅N₃O₂S₂ 

Relevant academic research and scientific papers

A selective modulator of peroxisome proliferator-activated receptor γwith an unprecedented binding mode

The nuclear peroxisome proliferator-activated receptor γhas well-validated therapeutic potential in metabolic, inflammatory, and neurodegenerative pathologies, but its activation is also associated with marked adverse effects and novel modes of PPARγmodulation are required. Here, we report the discovery and profiling of a new PPARγmodulator chemotype endowed with remarkable potency and a distinct binding mode in the orthosteric PPARγligand-binding site. Its R-enantiomer evolved as a eutomer regarding PPARγactivation with a high eudysmic ratio. The new PPARγmodulator revealed outstanding selectivity over the PPARα and PPARδsubtypes and did not promote adipogenesis in primary human fibroblasts, discriminating it from established agonists.

Metal-free synthesis of 2-mercaptobenzothiazoles and 6-(4-substituted-1H-1,2,3-triazol-1-yl)-2-mercaptobenzothiazoles via microwave-assisted synthesis pathway

A simple, efficient, and metal-free methodology for the preparation of 2-mercaptobenzothiazole and derivatives in excellent yields via microwave-assisted pathway is reported. Our condition provides a convenient protocol for the synthesis of a diverse collection of 2-mercaptobenzothiazoles and 6-(4-substituted-1H-1,2,3-triazol-1-yl)-2-mercaptobenzothiazoles with a very simple purification process. This report provides an alternative protocol for fast access to the wide range of compounds for sequence synthesis and biological studies.

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.

Synthesis and invitro Evaluation of West Nile Virus Protease Inhibitors Based on the 2-{6-[2-(5-Phenyl-4H-{1,2,4]triazol-3-ylsulfanyl)acetylamino]benzothiazol-2-ylsulfanyl}acetamide Scaffold

In recent years, clinical symptoms resulting from West Nile virus (WNV) infection have worsened in severity, with an increased frequency in neuroinvasive diseases among the elderly. As there are presently no successful therapies against WNV for use in humans, continual efforts to develop new chemotherapeutics against this virus are highly desired. The viral NS2B-NS3 protease is a promising target for viral inhibition due to its importance in viral replication and its unique substrate preference. In this study, a WNV NS2B-NS3 protease inhibitor with a 2-{6-[2-(5-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)acetylamino]benzothiazol-2-ylsulfanyl}acetamide scaffold was identified during screening. Optimization of this initial hit by synthesis and screening of a focused compound library with this scaffold led to the identification of a novel uncompetitive inhibitor (1a24, IC50=3.4±0.2μM) of the WNV NS2B-NS3 protease. Molecular docking of 1a24 into the WNV protease showed that the compound interferes with productive interactions of the NS2B cofactor with the NS3 protease and is an allosteric inhibitor of the WNV NS3 protease.

Discovering Small-Molecule Estrogen Receptor α/Coactivator Binding Inhibitors: High-Throughput Screening, Ligand Development, and Models for Enhanced Potency

Small molecules, namely coactivator binding inhibitors (CBIs), that block estrogen signaling by directly inhibiting the interaction of the estrogen receptor (ER) with coactivator proteins act in a fundamentally different way to traditional antagonists, which displace the endogenous ligand estradiol. To complement our prior efforts at CBI discovery by denovo design, we used high-throughput screening (HTS) to identify CBIs of novel structure and subsequently investigated two HTS hits by analogue synthesis, finding many compounds with low micromolar potencies in cell-based reporter gene assays. We examined structure-activity trends in both series, using induced-fit computational docking to propose binding poses for these molecules in the coactivator binding groove. Analysis of the structure of the ER-steroid receptor coactivator (SRC) complex suggests that all four hydrophobic residues within the SRC nuclear receptor box sequence are important binding elements. Thus, insufficient water displacement upon binding of the smaller CBIs in the expansive complexation site may be limiting the potency of the compounds in these series, which suggests that higher potency CBIs might be found by screening compound libraries enriched with larger molecules.

Compound and use

A compound contains a ligand group and at least one group of the general formula --XRn where X is a linking group which contains at least one hetero-atom, R is a saturated hydrocarbyl group containing at least six carbon atoms or is an unsaturated hydrocarbyl group containing at least three carbon atoms. The ligand group can be a polyhydroxyhydrocarbyl, a triazole, an imidazole, an indazole, a thiazole, an oxazole, a carbamate, an xanthate or a phthalazine. The compounds can be used to improve bonding between a metal and a coating material in contact with the metal surface. The metal may be a tire cord and the coating material rubber or a rubber composition.

Metal treatment

A compound containing a ligand group and a group of the general formula -NRCOR1aXbCR2=CHCOR3 is used for treatment of a metal. The ligand group can be a triazole, an imidazole, an indazole, a thiazole, an oxazole, a carbamate, an xanthate or a phthalazine, or derivatives thereof. The compounds can be coated onto a metal surface, for example a copper surface. The metal surface may also be coated, simultaneously or subsequently, with a surface coating composition such as a paint or lacquer or an adhesive. When used with an adhesive, an increase in the adhesive strength is achieved.