51618-29-2

Usage

Chemical Properties

Yellow solid

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

Upstream product

• 554-00-7 2,4-Dichloroaniline 
• 873-38-1 4-chloro-2-bromoaniline 
• 140-92-1 potassium isopropylxanthate 
• 75-15-0 carbon disulfide 
• 63069-48-7 p-chloro-o-iodoaniline 
• 31183-89-8 2-[(2-amino-5-chlorophenyl)dithio]-4-chlorophenylamine 
• 140-89-6 potassium ethyl xanthogenate 
• 106-47-8 4-chloro-aniline 
• 23474-98-8 2-amino-5-chlorobenzenethiol 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 35576-53-5 6-Chloro-1,2,3-benzodithiazol-1-ium chloride 
• 3507-17-3 6-chloro-2-bromobenzothiazole 
• 17356-08-0 thiourea 
• 2942-10-1 6-chloro-1,3-benzothiazole 

Downstream Products

• 3622-23-9 2,6-dichloro-1,3-benzothiazole 
• 99580-39-9 2-(benzylsulphanyl)-6-chloro-1,3-benzothiazole 
• 1189350-90-0 6-chloro-2-(phenylthio)-1,3-benzothiazole 
• 88946-22-9 6-chlorobenzothiazole-2-sulfenamide 
• 2727-38-0 {2-[3-chloro-4-(6-chloro-benzothiazol-2-ylsulfanylmethyl)-phenoxy]-ethyl}-diethyl-amine 
• 3905-87-1 {2-[4-(6-chloro-benzothiazol-2-ylsulfanylmethyl)-2-iodo-phenoxy]-ethyl}-diethyl-amine 
• 1857-73-4 {2-[3-(6-chloro-benzothiazol-2-ylsulfanylmethyl)-phenoxy]-ethyl}-diethyl-amine 
• 3951-07-3 {2-[2-(6-chloro-benzothiazol-2-ylsulfanylmethyl)-phenoxy]-ethyl}-diethyl-amine 
• 3507-42-4 6-chloro-2-(methylthio)benzo[d]thiazole 

Relevant academic research and scientific papers

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.

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.

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.

Metal sulfide: An efficient promoter for the synthesis of 2-mercaptobenzothiazoles from 2-haloanilines and carbon disulfide

A convenient method has been developed for the preparation of a variety of 2-mercaptobenzothiazoles from 2-haloanilines and CS2 mediated by metal sulfide. In this reaction, 2-haloanilines reacted with CS2 in the presence of Na2S · 9H2O to form 2-mercaptobenzothiazoles. Na2S · 9H2O functioned both as an activator of CS2 and as a base. Furthermore, NMR analysis was used to identify the different reaction mechanisms of 2-haloanilines and CS2 mediated by Na2S or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), which demonstrated that Na2S interacted only with CS2, while DBU reacted with both 2-iodoaniline and CS2.

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.

An efficient copper-catalyzed synthesis of 2-mercaptobenzothiazole through S-arylation/heterocyclization of 2-haloaniline with potassium xanthate

A mild and efficient methodology to produce 2-mercaptobenzothiazoles in DMF via ortho-haloaniline coupling with potassium O-ethyl dithiocarbonate catalyzed by copper without a ligand has been developed.

Green synthesis method of 2-mercaptobenzothiazoles derivatives

The invention provides a green synthesis method of 2-mercaptobenzothiazoles derivatives. The method comprises the step of enabling o-amino aromatic disulfide, CS2 and metal sulfide to be in contact with a solvent to obtain the 2-mercaptobenzothiazoles derivatives, wherein the solvent is at least one of water, low carbon alcohol, dimethyl sulfoxide (DMSO), dimethyl formamide (DMF), N-methyl pyrrolidone (NMP) and 1, 4-dioxane. Compared with the prior art, the method enables the o-amino aromatic disulfide to react with the CS2, thus rapidly and efficiently synthesizing the 2-mercaptobenzothiazoles derivatives; the raw materials used by the method are stable, easy to obtain and low in cost; the synthesis method is simple and convenient in operation, short in step, high in yield and easy in purification of a product.

Efficient, Iron-Catalyzed Synthesis of 2-Mercaptobenzothiazole Through S-Arylation/Heterocyclization of 2-Haloaniline with Potassium Xanthate

A mild and practical method for the synthesis of 2-mercaptobenzothiazole has been developed by using iron as an efficient catalyst. The present tandem reaction process allows access to a wide range of 2-mercaptobenzothiazoles in good to excellent yields by the reaction of 2-haloaniline with potassium O-ethyl dithiocarbonate in the presence of FeF3 as a catalyst and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl as a ligand under an atmosphere of argon.

Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from o-Iodoanilines, Isocyanide, and Potassium Sulfide

An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.

Analogues of the allosteric heat shock protein 70 (Hsp70) inhibitor, MKT-077, as anti-cancer agents

The rhodacyanine, MKT-077, has antiproliferative activity against cancer cell lines through its ability to inhibit members of the heat shock protein 70 (Hsp70) family of molecular chaperones. However, MKT-077 is rapidly metabolized, which limits its use as either a chemical probe or potential therapeutic. We report the synthesis and characterization of MKT-077 analogues designed for greater stability. The most potent molecules, such as 30 (JG-98), were at least 3-fold more active than MKT-077 against the breast cancer cell lines MDA-MB-231 and MCF-7 (EC50 values of 0.4 ± 0.03 and 0.7 ± 0.2 μM, respectively). The analogues modestly destabilized the chaperone clients, Akt1 and Raf1, and induced apoptosis in these cells. Further, the microsomal half-life of JG-98 was improved at least 7-fold (t1/2 = 37 min) compared to MKT-077 (t1/2 5 min). Finally, NMR titration experiments suggested that these analogues bind an allosteric site that is known to accommodate MKT-077. These studies advance MKT-077 analogues as chemical probes for studying Hsp70s roles in cancer.