37390-63-9

Usage

Uses

Used in Organic Synthesis:
6-BROMO-2-HYDRAZINO-1,3-BENZOTHIAZOLE is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of new chemical bonds and the creation of novel molecules with specific properties.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 6-BROMO-2-HYDRAZINO-1,3-BENZOTHIAZOLE is utilized as a building block for the development of new drugs and biologically active compounds. Its presence in a molecule can impart specific pharmacological activities, making it a valuable component in drug discovery and design.
Used in Chemical Production:
6-BROMO-2-HYDRAZINO-1,3-BENZOTHIAZOLE may also serve as an intermediate in the production of other chemical compounds, contributing to the synthesis of a wide range of products across different industries.
Safety Precautions:
As with any chemical substance, it is essential to follow proper handling and safety precautions when working with 6-BROMO-2-HYDRAZINO-1,3-BENZOTHIAZOLE. This includes using appropriate personal protective equipment, working in well-ventilated areas, and adhering to established safety guidelines to minimize potential risks and ensure a safe working environment.

InChI:InChI=1/C7H6BrN3S/c8-4-1-2-5-6(3-4)12-7(10-5)11-9/h1-3H,9H2,(H,10,11)

Upstream product

• 15864-32-1 2-amino-6-bromobenzothiazole 
• 2646-30-2 1-(4-bromophenyl)thiourea 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 37120-68-6 4-methyl-benzaldehyde (6-bromo-benzothiazol-2-yl)-hydrazone 
• 37120-59-5 benzaldehyde (6-bromo-benzothiazol-2-yl)-hydrazone 
• 37120-65-3 4-bromo-benzaldehyde (6-bromo-benzothiazol-2-yl)-hydrazone 
• 79403-47-7 C₁₄H₁₀Br₂N₄S₂ 
• 1246493-40-2 3-(3-pyridyl)-5-(4-methylphenyl)-4-(N-(6-bromo-1,3-benzothiazol-2-yl)amino)-4H-1,2,4-triazole 
• 1268376-07-3 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-6-bromo-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole 
• 1316270-36-6 C₂₀H₁₂BrN₇O₂S 
• 1384203-29-5 3-(3-pyridyl)-5-(4-chlorophenyl)-4-(N-6-bromo-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole 
• 1135869-06-5 2-chloro-5-(5-(1-(2-(6-bromobenzothiazol-2-yl)hydrazono)ethyl)furan-2-yl)benzoic acid 

Relevant academic research and scientific papers

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones

We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, 1H NMR, 13C NMR, and HRMS) techniques. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, 4e (IC50 = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC50 = 9.35 μg/mL) and 4i (IC50 = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC50 = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives 4e and 4o, respectively. [Figure not available: see fulltext.].

Phthaloyl Dichloride–DMF Mediated Synthesis of Benzothiazole-based 4-Formylpyrazole Derivatives: Studies on Their Antimicrobial and Antioxidant Activities

Benzothiazole-based pyrazole derivatives prepared by a molecular hybridization approach with an aim to influence the biological activity significantly. Efficient conversion of hydrazones 3a–k derived from their corresponding methyl ketones to 4-formylpyrazoles 4a–k was carried out at 60°C in dioxane, using the Vilsmeier–Haack reagent isolated from phthaloyl dichloride and N,N-dimethylformamide. The newly synthesized compounds 4a–k and hydrazones 3a–k were screened in vitro for their antimicrobial activities using the broth macrodilution method. The compounds 4a–k were also screened for their antioxidant activities using the DPPH radical scavenging assay. Some of the synthesized compounds showed significant antibacterial and antifungal activities as evident from their minimum inhibitory concentrations. Compound 4d showed remarkable antioxidant activity.

Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists

Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ-induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a-h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR-γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side-effects.

Discovery of potent and selective benzothiazole hydrazone inhibitors of Bcl-XL

Developing potent molecules that inhibit Bcl-2 family mediated apoptosis affords opportunities to treat cancers via reactivation of the cell death machinery. We describe the hit-to-lead development of selective Bcl-X L inhibitors originating from a high-throughput screening campaign. Small structural changes to the hit compound increased binding affinity more than 300-fold (to IC50 w L. Surface plasmon resonance experiments afford strong evidence of binding affinity within the hydrophobic groove of Bcl-XL. Biological experiments using engineered Mcl-1 deficient mouse embryonic fibroblasts (MEFs, reliant only on Bcl-XL for survival) and Bax/Bak deficient MEFs (insensitive to selective activation of Bcl-2-driven apoptosis) support a mechanism-based induction of apoptosis. This manuscript describes the first series of selective small-molecule inhibitors of Bcl-XL and provides promising leads for the development of efficacious therapeutics against solid tumors and chemoresistant cancer cell lines.

Synthesis of 1,2,4-triazole derivatives containing benzothiazoles as pharmacologically active molecule

In attempt to make significant pharmacologically active molecule, we report here the synthesis and in vitro antimicrobial and antitubercular activity of various series of 3-(3-pyridyl)-5-(4-nitrophenyl)-4-(N-substituted-1,3- benzothiazol-2-amino)-4H-1,2,4-triazole. The antimicrobial activity of title compounds were examined against two Gram-positive bacteria (Staphylococcus aureus, Streptococcus pyogenes), two Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), and three fungi (Candida albicans, Aspergillus niger, Aspergillus clavatus) using the broth microdilution method and antitubercular activity H37Rv using Lowenstein-Jensen agar method.

Antimycobacterial and antimicrobial study of new 1,2,4-triazoles with benzothiazoles

In this study, we report the antimycobacterial and antimicrobial evaluation of newly synthesized 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-substituted-1,3- benzothiazol-2-amino)-4H-1,2,4-triazole 6a-j in good yields. All the synthesized compounds have been established by elemental analysis, IR, 1H NMR, 13C-NMR and Mass spectral data. In-vitro antimycobacterial activity was carried out against (Mycobacterium tuberculosis) H37Rv strain using Lowenstein-Jensen medium and antimicrobial activity against two Gram positive bacteria (Staphylococcus aureus, Streptococcus pyogenes), two Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and three fungal species (Candida albicans, Aspergillus niger, Aspergillus clavatus) using the broth microdilution method. Compounds 2e, 6a, 6g, 6h, and 6j exhibited promising antimicrobial activity whereas compound 6j showed very good antimycobacterial activity. The antimycobacterial and antimicrobial evaluation of newly synthesized 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-substituted-1,3-benzothiazol- 2-amino)-4H-1,2,4-triazoles is reported in detail. Compounds 2e, 6a, 6g, 6h, and 6j exhibited promising antimicrobial activity whereas compound 6j showed very good antimycobacterial activity. Copyright

Pharmacological evaluation and characterizations of newly synthesized 1,2,4-triazoles

The triazole analogs were obtained via. multistep synthesis sequence beginning with ethyl nicotinoate 3 which on treatment with hydrazine hydrate yields nicotinoyl hydrazide 4. Intermolecular cyclisation of 4 with 4-methylbenzoic acid in presence of phosphorous oxy chloride affords 2-(3-pyridyl)-5-(4-methylphenyl)-1,3,4-oxadiazole 5. Condensation of 5 with various substituted 2-hydrazino benzothiazole 2a-j results in 3-(3-pyridyl)-5-(4-methylphenyl)-4-(N-substituted-1,3-benzothiazol-2-amino) -4H-1,2,4-triazole 6a-j analogs. All the compounds have been characterized by elemental analysis, IR, 1H NMR, 13C NMR and mass spectral data. In vitro antitubercular activity was carried out against Mycobacterium tuberculosis H37Rv strain using Lowenstein-Jensen medium and antimicrobial activity against various bacteria and fungi using broth microdilution method. Compounds 2e, 6a, 6b, 6c, 6d, 6g, 6h and 6i emerged as promising antimicrobials. It was also observed that the promising antimicrobials have proved to be better antituberculars. Compound 6j showed better antitubercular activity compared to rifampicin. 3-(3-Pyridyl)-5-(4-methylphenyl) -4-(N-substituted-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole 6a-j were synthesized and their antitubercular activity against H37Rv and antimicrobial activities have been tested.

Synthesis and antimicrobial activity of 2-(6-substituted-1,3-benzothiazol- 2-yl)-N-(4-halophenyl)hydrazinecarbothioamide

A number of new 2-(6-substituted-1,3-benzothiazol-2-yl)-N-(4-halophenyl) hydrazinecarbothioamide (5a-o) have been synthesized and screened for antibacterial activity.

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.