20174-68-9

Basic information

• Product Name: 4-Methyl-2-benzothiazolehydrazine
• Synonyms: 4-METHYL-2-HYDRAZINO BENZOTHIAZOLE;4-methylbenzothiazol-2(3H)-one hydrazone;2-hydrazin-4-methylbenzothiazole;4-METHYL-2(3H)-BENZOTHIAZOLONE YDRAZONE;2(3H)-Benzothiazolone,4-methyl-,hydrazone(9CI);4-METHYL-2(3H)-BENZOTHIAZOLONEHYDRAZONE;4-Methyl-2-benzothiazolehydrazine;4-METHYL-2(3H)-BENZOTHIAZOLONHYDRAZONE
• CAS NO: 20174-68-9
• Molecular Formula: C₈H₉N₃S
• Molecular Weight: 179.24216
• EINECS: 243-562-4
• Product Categories: BENZOTHIAZOLE;Thiazoles;white or white-like crystal
• Mol File: 20174-68-9.mol

Chemical Properties

• Melting Point: 167-169 °C
• Boiling Point: 340.3 °C at 760 mmHg
• Flash Point: 159.6 °C
• Appearance: /
• Density: 1.387g/cm³
• Vapor Pressure: 8.68E-05mmHg at 25°C
• Refractive Index: 1.774
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• PKA: 2.62±0.20(Predicted)
• CAS DataBase Reference: 4-Methyl-2-benzothiazolehydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-2-benzothiazolehydrazine(20174-68-9)
• EPA Substance Registry System: 4-Methyl-2-benzothiazolehydrazine(20174-68-9)

Safety Data

• Hazardous Substances Data: 20174-68-9(Hazardous Substances Data)

Usage

Uses

2-Hydrazino-4-methylbenzothiazole is used in the synthesis of pesticides.

InChI:InChI=1/C8H9N3S/c1-5-3-2-4-6-7(5)10-8(11-9)12-6/h2-4H,9H2,1H3,(H,10,11)

Upstream product

• 3622-32-0 2-chloro-4-methyl-benzothiazole 
• 1477-42-5 4-methyl-1,3-benzothiazol-2-amine 
• 53065-21-7 2-amino-4-methylbenzothiazole hydrobromide 
• 95-53-4 o-toluidine 
• 614-78-8 o-tolylthiourea 
• 2644-70-4 hydrazine hydrochloride 
• 53065-25-1 4-Methyl-2-dimethylaminobenzothiazole hydrobromide 
• 64036-72-2 4-methyl-2-aminobenzothiazole hydrochloride 
• 3622-20-6 4-methyl-2-methylsulfanyl-1,3-benzothiazole 
• 2268-77-1 2-Mercapto-4-methyl-benzothiazole 
• 53848-17-2 2-bromo-6-methylaniline 

Downstream Products

• 3622-32-0 2-chloro-4-methyl-benzothiazole 
• 41814-78-2 5-methyl-1,2,4-triazolo[3,4-b]benzothizole 
• 219904-17-3 2-acetylhydrazino-4-methylbenzothiazole 
• 219904-19-5 3-(3-bromo-2-phenyl-propenyl)-5-methyl-benzo[4,5]thiazolo[2,3-c][1,2,4]triazole 
• 1246493-45-7 3-(3-pyridyl)-5-(4-methylphenyl)-4-(N-(4-methyl-1,3-benzothiazol-2-yl)amino)-4H-1,2,4-triazole 
• 1268376-12-0 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-4-methyl-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole 
• 1316270-44-6 C₂₁H₁₅N₇O₂S 

Relevant articles and documents

The syntheses and crystal structure of novel 5-methyl-3-substituted-1,2,4-triazolo[3,4-b]benzothiazoles

Novel 5-methyl-3-substituted-1,2,4-triazolo[3,4-b]benzothiazoles were synthesized from o-methylaniline to 5 with various aromatic carbonic acids. The yielded product 6a-e were confirmed by Elemental Analyses, NMR, MS, IR spectra and 6e was investigated with X-ray crystallography. Compound 6e, C24H16N4S, Mr = 392.69, crystallized in the triclinic space group P1? with unit cell parameters a = 9.713(3) ?, b = 14.645(4) ?, c = 15.641(3) ?, α = 113.17(2)°, β=90.11(2)°, γ = 109.29(2)°, V = 1908.1(7) ?3, Z = 4, Dm = 1.366 Mgm-3.

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.

Method for synthesizing 4-methyl-2-benzothiazolehydrazine

The invention discloses a method for synthesizing 4-methyl-2-benzothiazolehydrazine. The method comprises the following steps: carrying out synthesis reaction on o-toluidine and thiocyanate in acid toobtain o-tolylthiourea; carrying out a synthesis reaction on the o-tolylthiourea and a catalyst in water to obtain 2-amino-4-methylbenzothiazole; and carrying out a synthesis reaction on the 2-amino-4-methylbenzothiazole in hydrazine hydrate, so as to obtain the 4-methyl-2-benzothiazolehydrazine. The method for synthesizing the 4-methyl-2-benzothiazolehydrazine, provided by the invention, is simple to operate, less in three wastes, capable of repeatedly applying wastewater, high in product content, good in quality and suitable for industrial mass production.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

Production process for 4-methyl-2-hydrazinobenzothiazole

4-methyl-2-hydrazinobenzothiazole is an important intermediate for synthesis of tricyclazole, and the tricyclazole is a main drug for preventing and controlling rice blast and a high-efficiency systemic fungicide, and has high biological activity, a unique action mechanism and special effects on preventing and controlling the rice blast. A current synthetic technology has low reaction efficiency and not high product purity, and produces more three industrial waste (waste water, waste gas and solid waste). The invention overcomes the above disadvantages to provide a production process for the 4-methyl-2-hydrazinobenzothiazole; and the process is realized through the following steps: 1, weighing raw materials for standby application; 2, performing an addition reaction to synthesize o-methylphenyl-thiourea; 3, performing a ring-closure reaction to synthesize 4-methyl-2-aminobenzothiazole hydrochloride; 4, performing a substitution reaction to synthesize the 4-methyl-2-hydrazinobenzothiazole; and 5, performing drying and performing packaging.

Preparing method for modified 2-hydrazinobenzothiazole

The invention discloses a preparing method for modified 2-hydrazinobenzothiazole. According to the preparing method, substituted aniline is catalyzed through hydrobromic acid to obtain the 2-aminobenzothiazole hydrobromide, the 2-aminobenzothiazole hydrobromide is directly put into a following replacement reaction, other acid does not need to be added for catalysis, and the obtained yield is high. The acid-base using amount in the whole reaction process is reduced, generation of waste gas, wastewater and solid waste is reduced, and the environment-friendly-production aim is achieved.

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.

Synthesis of 4-methyl-2- [...] method of and thiazole

The invention discloses a method for synthesizing 4-methyl-2-diazanyl benzothiazole. The method comprises the steps of taking 4-methyl-2-amino benzothiazole as a raw material, adding hydrazine hydrate into a pressure container containing a hydrochloric acid water solution and performing a heating reaction in the presence of an emulsifying agent or not, so as to obtain a final product 4-methyl-2-diazanyl benzothiazole. By applying a hydrazine water reaction system mechanically, losses of raw materials and energy can be reduced effectively; the method has the advantages of greatly reducing the amount of the used hydrazine, satisfying the green chemistry conception, being applicable to industrial production and the like; the method is simple and convenient to operate in process, simple in after treatment and applicable to industrial popularization, and has good social benefit and economic benefit.

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.

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.