3507-41-3

Usage

Uses

Used in Pharmaceutical Industry:
Benzothiazole, 5-chloro-2-(methylthio)(7CI,8CI,9CI) is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, Benzothiazole, 5-chloro-2-(methylthio)(7CI,8CI,9CI) is utilized as a key component in the formulation of pesticides and other crop protection agents. Its properties contribute to the effectiveness and stability of these products, ensuring better crop yield and protection against pests.
Used in Rubber Chemical Industry:
Benzothiazole, 5-chloro-2-(methylthio)(7CI,8CI,9CI) is employed as a performance-enhancing additive in the rubber chemical industry. It improves the physical and chemical properties of rubber, such as resistance to heat, oxidation, and corrosion, making it suitable for various applications, including automotive, industrial, and consumer products.
Used in Dyes:
As a component in dyes, Benzothiazole, 5-chloro-2-(methylthio)(7CI,8CI,9CI) contributes to the color intensity and stability of the dyes. Its presence in dye formulations can enhance the performance and durability of colored products in various industries, such as textiles, plastics, and printing inks.
Used in Antioxidants:
Benzothiazole, 5-chloro-2-(methylthio)(7CI,8CI,9CI) is used as an antioxidant in various applications, including plastics, rubber, and coatings. Its ability to scavenge free radicals and prevent oxidative degradation helps to extend the service life and maintain the quality of these materials.
Used in Corrosion Inhibitors:
In the field of corrosion inhibition, Benzothiazole, 5-chloro-2-(methylthio)(7CI,8CI,9CI) is utilized as an active ingredient in corrosion inhibitors for metals. Its presence in these formulations helps to protect metal surfaces from corrosion, ensuring the longevity and integrity of metal structures and components in various industries, such as oil and gas, construction, and automotive.

Upstream product

• 5331-91-9 5-chloro-1,3-benzothiazole-2(3H)-thione 
• 74-88-4 methyl iodide 
• 5331-91-9 5-chloro-2-mercaptobenzothiazole 
• 77-78-1 dimethyl sulfate 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 95-82-9 2,5 dichloroaniline 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 20600-44-6 5-chloro-1,3-benzothiazol-2(3H)-one 
• 20174-72-5 (5-chloro-1,3-benzothiazol-2-yl)hydrazine 
• 1279099-66-9 2-(5-chlorobenzothiazol-2-yl)-1,2-dihydro-5-phenyl-3H-pyrazol-3-one 
• 1452793-11-1 2-(5-chlorobenzothiazol-2-yl)-4-[1-dimethylaminomethylidene]-5-phenyl-2,4-dihydropyrazol-3-one 
• 1452793-08-6 4-[1-aminomethylidene]-2-(5-chlorobenzothiazol-2-yl)-5-phenyl-2,4-dihydropyrazol-3-one 

Relevant academic research and scientific papers

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.

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.

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.

AMINOMETHYLENE PYRAZOLONES WITH THERAPEUTIC ACTIVITY

A compound having the structure according to formula III wherein: X is NH or S;R1 is H or (1C-4C)alkyl;R2 is (1C-4C)alkyl, phenyl or a monocyclic aromatic ring having one or more N-, O-or S-atoms in the ring, which alkyl, phenyl or aromatic ring is optionally substituted with one or more groups selected from (1C-4C)alkyl, (1C-4C)alkyloxy, halo(1C-4C)alkyl, halo(1C-4C)alkyloxy, phenyloxy, phenylthio, halogen, or nitro;R3 and R4 are each independently H, (1C-6C)alkyl, (2C-6C) alkenyl, (2C-6C)alkynyl, cyano, (3C-6C)cycloalkyl, phenyl, a monocyclic aromatic ring having one or more N-, O- or S-atoms in the ring, a monocyclic non-aromatic ring having one or more N-, O- or S-atoms in the ring, each optionally substituted with hydroxyl, (1C-4C)alkoxy, phenyl, cycloalkyl, piperidyl, piperazinyl, furyl, thienyl, pirazinyl, pyrrolyl, 2H-pyrrolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyrrolidonyl, pyrrolinyl, imidazolinyl, imidazolyl, a monocyclic aromatic ring having one or more N-, O- or S- atoms in the ring, whereby each of these optional substituents is optionally further substituted with (1C-4C)alkyl, (1C-4C)alkyloxy, halo(1C-4C)alkyl, halo(1C-4C)alkyloxy, halogen, nitro or (1C-2C)dioxol forming a ring;or R3 and R4 form together pyrrolyl, imidazolyl, pyrazolyl, pyrrolidinyl, pyrrolinylimidazolidinyl, imidazolinyl, piperidyl, piperazinylmorpholinyl, each optionally substituted with (1C-6C)alkyl, phenyl(1C-4C)alkyl, phenylketo(1C-4C)alkyl; R5 is H, Cl, F, Br, Me, NO2, t-butyl, OCF3, OCH3, CF3; R6 is H, (1C-4C)alkyl, (1C-4C)alkyloxy, halo(1C-4C)alkyl, halo(1C-4C)alkyloxy, nitro or halogen;R7 is H,F, Cl, Br, Me, NO2, t-butyl, OCF3, OCH3, CF3; or pharmaceutically acceptable addition salts thereof for use in treatments of carcinoma, in particular to delay, prevent or reverse metastasis in prostate cancer.

Synthesis of chloro-substituted analogs of Thiazole orange - Fluorophores for flow cytometric analyses

Synthesis, absorption and fluorescence properties of a series of asymmetrical monomethine cyanine dyes, chloro-containing analogs of Thiazole orange, are reported. Their staining ability was studied by flow cytometry. The saturating concentrations of each dye that gives a stable staining intensity have been determined. The ability of dyes B9, B11, B13 to stain live macrophages and apoptotic splenocytes was investigated. Positive signal in nucleus of adherent macrophages detected by fluorescent microscopy showed good specificity of B9, B11 and B13 dyes for DNA. In apoptotic assay cells positive for Annexin V were stained more brightly with the dyes B9, B11 and B13 than with propidium iodide. Despite that B13 showed high DNA selectivity it induces apoptosis of splenocytes and it is not suitable for detection of dead cells. The other synthesized chloro-containing analogs of Thiazole orange B9 and B11 can be successfully used for flow cytometric analyses of DNA content in live cells and for analyses of cell apoptosis.

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.

An easy and fast ultrasonic selective S-alkylation of hetaryl thiols at room temperature

A series of 2-alkylthio derivatives of hetaryl thiols were synthesized by selective S-alkylation with alkyl halides (bromides and iodides) with ultrasonic irradiation at room temperature. The reaction was found to be generally applicable to hetaryl thiol derivatives with different substituents in the aromatic nucleus and various alkyl halides. The reaction gives high to excellent yields of products with high purity.

2-[3H-THIAZOL-2-YLIDINEMETHYL]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE

The present invention pertains to certain 2-[3H-thiazol-2-ylidinemethyl]pyridine compounds and analogs thereof, which, inter alia, inhibit cell proliferation, treat cancer, etc., and more specifically to compounds of the following formula, wherein RA1, RA2, RA3, RA4, RB1, RB2, RNA, RNB, and X? are as defined herein: The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit cell proliferation, and in the treatment of proliferative conditions such as cancer, etc.

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.

Structure modifications of 6-aminoquinolones with potent anti-HIV activity

We have recently discovered that 6-aminoquinolone derivatives could be valid leads for the development of new anti-HIV agents because of their new and diversified mode of action. In fact, studies carried out on the lead WM5 showed that this derivative is