3507-26-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-methylbenzothiazole is used as a reactant and reagent for the synthesis and preparation of benzothiazole-based compounds. Specifically, it is utilized in the development of benzothiazole-π-piperazine derivatives, which serve as second-generation Non-Covalent NAAA Inhibitors. These inhibitors are designed to treat multiple sclerosis (MS) and other chronic disorders by targeting the NAAA enzyme, which plays a crucial role in the pathogenesis of these conditions.
Used in Chemical Synthesis:
As a versatile chemical compound, 2-Chloro-6-methylbenzothiazole is also used as an intermediate in the synthesis of various other organic compounds. Its unique structure allows it to be a valuable building block for creating a wide range of molecules with different properties and applications.
Used in Research and Development:
Due to its unique chemical properties and potential applications, 2-Chloro-6-methylbenzothiazole is often employed in research and development settings. Scientists and researchers use 2-Chloro-6-methylbenzothiazole to explore new chemical reactions, develop novel synthetic methods, and investigate its potential applications in various fields, including pharmaceuticals, materials science, and environmental chemistry.

InChI:InChI=1/C8H6ClNS/c1-5-2-3-6-7(4-5)11-8(9)10-6/h2-4H,1H3

Upstream product

• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 10026-13-8 phosphorus pentachloride 
• 20174-69-0 2-hydrazino-6-methylbenzothiazole 
• 2268-79-3 2-mercapto-6-methylbenzothiazole 
• 583-68-6 2-bromo-p-toluidine 
• 106-49-0 p-toluidine 
• 75-15-0 carbon disulfide 

Downstream Products

• 101281-22-5 methyl-(6-methyl-benzothiazol-2-yl)-p-tolyl-amine 
• 67058-58-6 6-methyl-2-phenylamino-1,3-benzothiazole 
• 85063-56-5 N-(4-ethoxyphenyl)-6-methylbenzo[d]thiazol-2-amine 
• 78072-95-4 methyl-(6-methyl-benzothiazol-2-yl)-phenyl-amine 
• 2369-32-6 6-methyl-N-(4-fluorophenyl)benzo[d]thiazol-2-amine 
• 85063-54-3 (N-(4-bromophenyl)-6-methylbenzo[d]thiazol-2-amine) 
• 791594-39-3 (4-iodo-phenyl)-(6-methyl-benzothiazol-2-yl)-amine 
• 2268-79-3 6-methyl-1,3-benzothiazole-2(3H)-thione 
• 78073-02-6 2-o-tolylimino-6-methylbenzothiazoline 
• 78073-00-4 2-o-tolylamino-3,6-dimethylbenzothiazoline 
• 3507-35-5 6-methyl-2-(methylthio)benzo[d]thiazole 
• 78072-99-8 (3,6-dimethyl-3H-benzothiazol-2-ylidene)-phenyl-amine 
• 2268-79-3 2-mercapto-6-methylbenzothiazole 
• 20174-69-0 2-hydrazino-6-methylbenzothiazole 

Relevant academic research and scientific papers

Water-Promoted Chlorination of 2-Mercaptobenzothiazoles

Substituted benzothiazoles play an important role in medicinal chemistry due to their pharmacological properties. Their 2-substituted derivatives are often prepared from 2-chlorobenzothiazoles, which in turn can be synthesized from the 2-mercapto precursor using sulfuryl chloride. In practice, this seemingly straightforward and widely used reaction can be impeded by poor reproducibility and low reaction yields. In this communication, we report that the simple addition of water to the reaction leads to remarkable improvements in reaction efficiency. We attribute this effect to the formation of acid through partial hydrolysis of sulfuryl chloride. This hypothesis is supported by the observation that improved yields were also obtained in the presence of some anhydrous acidic additives. The simple combination of sulfuryl chloride and water reproducibly provides excellent yields for a range of chlorinated products.

Synthesis and antibacterial evaluation of a novel series of 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazoles

The 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazole scaffold was selected as a central core structure for the discovery of novel antibacterial compounds. A systematic variation of the substituents on the oxo-pyrazole moiety, as well as on the benzo moiety, led to the creation of a small and focused library of benzothiazoles that was subjected to antibacterial screening. In a first round of screening, activity of the compounds against six representative microorganisms was established. For the most potent congeners, MIC values against S. aureus and P. aeruginosa were determined. The structure-activity relationship study clearly revealed that subtle structural variations influence the antibacterial activity to a large extent. The most potent congeners displayed MIC values of 3.30 μM.

Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles

In this work, we report the synthesis and characterization of new compounds derived from benzothiazoles and thiadiazoles. We observed that structural modifications on these skeletons affected the antioxidant activity. Thiol and aminothiol compounds derived from thiadiazoles and benzothiazoles showed an interesting antioxidant property. The radioprotective activity has also been evaluated in mice. Some of these compounds could be good radioprotectors.

NOVEL PIPERAZINES, PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF

Disclosed are novel piperazine derivatives that act as agonists of the α7 nAChR. Also disclosed are phannaceutical compositions, methods of treating inflammatory conditions, methods of treating CNS disorders, methods for inhibiting cytokine release from mammalian cells and methods for the preparation of the novel compounds.

Ferulic acid and benzothiazole dimer derivatives with high binding affinity to β-amyloid fibrils

New ferulic acid and benzothiazole dimer derivatives were synthesized and evaluated by in vitro competition assay using [125I]TZDM for their specific binding affinities to Aβ fibrils. In particular, 4a showed the most excellent binding affinity (Ki = 0.53 nM), compared to PIB (Ki = 0.77 nM), for benzothiazole binding sites of Aβ1-42 fibrils. This result suggests a possibility of a potential AD diagnostic probe for detection of Aβ fibrils.

Preparation and use of aryl alkyl acid derivatives for the treatment of obesity

This invention relates to certain aryl alkyl acid compounds, compositions, and methods for treating or preventing obesity and related diseases.

QSAR study on H3-receptor affinity of benzothiazole derivatives of thioperamide

Starting from the structure of thioperamide, a known H3-antagonist, a new series of compounds with a benzothiazole nucleus instead of the cyclohexylcarbothioamide moiety was synthesized. Various substituents, selected by experimental design, were introduced in position 6 of the benzothiazole nucleus, in order to change its physico-chemical characteristics. The lipophilicity of the synthesized compounds was measured by means of RP-HPLC, and their H3-receptor affinity was evaluated by competitive binding assays on rat cortex synaptosomes, with the labelled ligand N(α)-[3H]methylhistamine. A QSAR analysis was performed on the experimental data, using also substituent constants taken from the literature. The newly synthesized compounds showed lower H3-affinities than thioperamide; quantitative structure-activity relationships, described by models obtained with PLS and MRA techniques, were observed among benzothiazole derivatives. According to these relationships, any attempt to improve the potency of these compounds should involve the substitution of the benzothiazole moiety with less bulky and/or more flexible structures, which should also be less lipophilic and allow better electronic interactions with the binding site. 1-(Benzothiazol-2-yl)-4-[(1H)-imidazol-4-yl]piperidine represents a limit structure for H3-activity, since it seems impossible to improve its affinity by means of substitution in the studied position of the benzothiazole nucleus, as shown by predictions performed by a PLS model.