5331-91-9

Usage

Uses

Used in Chemical Analysis:
5-Chloro-2-mercaptobenzothiazole is used as an analytical reagent for the detection and analysis of lipopolysaccharide through negative-ion matrix-assisted laser desorption ionization-time of flight mass spectrometry. It is also utilized in the analysis of high mannose N-linked glycans, where it has been found to be more sensitive than DHB (2,5-dihydroxybenzoic acid).
Used in Synthesis of Complex Compounds:
In the field of synthesis, CMBZT is used as a ligand in the formation of new mixed ligand silver(I) chloride complexes. One such example is the synthesis of a complex with the heterocyclic thioamide CMBZT and tri(p-tolyl)phosphine, which has potential applications in various areas.
Used in Analysis of Peptidoglycan Muropeptides:
5-Chloro-2-mercaptobenzothiazole is also employed in the analysis of peptidoglycan muropeptides, which are essential components of bacterial cell walls. This application contributes to the understanding of bacterial cell wall structure and function, as well as the development of new antibiotics targeting these structures.

InChI:InChI=1/C7H4ClNS2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)

Upstream product

• 95-82-9 2,5 dichloroaniline 
• 140-89-6 potassium ethyl xanthogenate 
• 75-15-0 carbon disulfide 
• 29124-55-8 2-amino-4-chlorophenyl disulfide 
• 2786-51-8 5-chlorobenzo[d]thiazole 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 128-04-1 sodium dimethyldithiocarbamate 
• 137-26-8 Thiram 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 6828-35-9 5-chloro-2-iodoaniline 
• 103-72-0 phenyl isothiocyanate 
• 89-61-2 2,5-dichloronitrobenzene 

Downstream Products

• 39883-96-0 3-[(5-chloro-2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoic acid methyl ester 
• 39883-95-9 3-[(5-chloro-2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoic acid ethyl ester 
• 23002-90-6 5-chloro-3-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-3H-benzothiazole-2-thione 
• 66858-94-4 5-chloro-3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-3H-benzothiazole-2-thione 
• 23002-93-9 5-chloro-3-(4-fluoro-anilinomethyl)-3H-benzothiazole-2-thione 
• 3507-41-3 5-Chloro-2-(methylthio)benzothiazole 
• 750621-60-4 C₁₅H₁₀ClNOS₂ 
• 796986-96-4 C₁₅H₉BrClNOS₂ 
• 522593-60-8 C₁₅H₉ClFNOS₂ 
• 832130-15-1 C₁₆H₁₂ClNO₂S₂ 

Relevant academic research and scientific papers

Optimization of Benzothiazole and Thiazole Hydrazones as Inhibitors of Schistosome BCL-2

Limited therapeutic options are available for the treatment of human schistosomiasis caused by the parasitic Schistosoma flatworm. The B cell lymphoma-2 (BCL-2)-regulated apoptotic cell death pathway in schistosomes was recently characterized and shown to share similarities with the intrinsic apoptosis pathway in humans. Here, we exploit structural differences in the human and schistosome BCL-2 (sBCL-2) pro-survival proteins toward a novel treatment strategy for schistosomiasis. The benzothiazole hydrazone scaffold previously employed to target human BCL-XL was repurposed as a starting point to target sBCL-2. We utilized X-ray structural data to inform optimization and then applied a scaffold-hop strategy to identify the 5-carboxamide thiazole hydrazone scaffold (43) with potent sBCL-2 activity (IC50 30 nM). Human BCL-XL potency (IC50 13 nM) was inadvertently preserved during the optimization process. The lead analogues from this study exhibit on-target activity in model fibroblast cell lines dependent on either sBCL-2 or human BCL-XL for survival. Further optimization of the thiazole hydrazone class is required to exhibit activity in schistosomes and enhance the potential of this strategy for treating schistosomiasis.

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

A facile and effective C–H functionalization strategy for the synthesis of 2-mercaptobenzothiazoles and 2-mercaptobenzoxazoles is described. 1,3-Propanedithiol was employed to convert benzothiazoles and benzoxazoles to the corresponding heteroarylthiols in the presence of potassium hydroxide and DMSO. This novel protocol is featured by direct C–H mercaptalization of heteroarenes and a simple reaction system.

Preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as mercapto source

The invention belongs to the synthesis field of medicine chemical intermediate, and provides a preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as a mercapto source. According to the preparation method, under inert gas protection, in dimethyl sulphoxide solvent, substituted benzoxazole(thiazole) and 1,3-dimercaptopropane are subjected to 120 to 140 DEG Cheating stirring in the presence of an alkali, after 12 to 24h of reaction, an obtained reaction solution is cooled to room temperature, and is subjected to acidifying post-treatment so as to obtaina product. The reaction conditions are simple; function group compatibility is excellent; yield is relatively high; the obtained 2-mercaptobenzoxazole(thiazole) compounds are important organic synthesis intermediates; application range in the field of chemical raw material, pesticide, and medicine is wide; and practical value and social and economic benefit are excellent.

AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate

A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercapto benzoheterocycles (2-mercapto benzothiazoles, benzoxazoles and benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional molecules with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This novel synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple experimental procedures.

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.

Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water

An efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-arylthiobenzoxazoles. Inexpensive metal catalyst and ligand, mild reaction temperature, and water as solvent make this protocol practically valuable and useful in organic synthesis.

Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: Metal sulfide-disulfide dynamic interchange reaction

A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS2 mediated by a metal sulfide in water is described. This synthetic methodology could be used to prepare diverse 2-mercaptobenzothiazole derivatives in good to excellent yields. In this paper, the concept of metal sulfide-disulfide dynamic interchange reaction was put forward. Then the intermediates of the interchange reaction between NaHS and a disulfide were detected by LC-MS, which demonstrated that the S-S bond of the disulfide could be broken by the metal sulfide through the dynamic interchange reaction. In addition, NaHS was eventually transformed into sulfur S8 by the dynamic interchange reaction. Moreover, the underlying mechanism of 2-mercaptobenzothiazole formation is proposed, in which NaHS not only acts as an S-S bond cleaving agent but also as an activator of CS2. As a result, a novel synthetic route for the preparation of sulfur-containing heterocycles from a disulfide is developed.

Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of novel benzothiazole-triazole derivatives

Benzothiazole-triazole derivatives 6a–6s have been synthesized and characterized by1H-NMR and13C-NMR. All synthetic compounds were screened for their in vitro α-glucosidase inhibitory activity by using Baker’s yeast α-glucosidase enzyme. The majority of compounds exhibited a varying degree of α-glucosidase inhibitory activity with IC50 values between 20.7 and 61.1 μM when compared with standard acarbose (IC50 = 817.38 μM). Among the series, compound 6s (IC50 = 20.7 μM) bearing a chlorine group at the 5-position of the benzothiazole ring and a tert-butyl group at the para position of the phenyl ring, was found to be the most active compound. Preliminary structure-activity relationships were established. Molecular docking studies were performed to predict the binding interaction of the compounds in the binding pocket of the enzyme.

An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water

An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.