20174-69-0

Usage

Uses

Used in Pharmaceutical Industry:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is used as a pharmaceutical precursor for the development of new drugs, leveraging its antimicrobial and anticancer properties. Its potential in drug development is being evaluated for the treatment of various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is used as a chemical intermediate for the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products.
Used in Dye Industry:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is utilized as a building block in the synthesis of dyes, where its unique structure can contribute to the creation of novel dyes with specific properties.
Used as a Corrosion Inhibitor:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is employed as a corrosion inhibitor in various industrial applications, where its chemical properties help to prevent the corrosion of metals, thereby extending the lifespan of equipment and structures.
Used in Antimicrobial Applications:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is used as an antimicrobial agent, which can be incorporated into products to prevent the growth of bacteria and other microorganisms, offering potential benefits in healthcare and other industries where microbial control is essential.
Used in Anticancer Applications:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is also being studied for its potential use as an anticancer agent, where it may contribute to the development of new therapeutic strategies against cancer.

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

Upstream product

• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 622-52-6 p-methylphenylthiourea 
• 106-49-0 p-toluidine 
• 3507-26-4 2-chloro-6-methylbenzo[d]thiazole 
• 622-52-6 p-tolyl thiocarbamide 
• 540-23-8 p-toluidine hydrochloride 

Downstream Products

• 122500-88-3 6-Methyl-2-pyrazol-1-yl-benzothiazole 
• 131501-46-7 C₁₂H₁₈N₄O₂P₂S 
• 124-40-3 dimethyl amine 
• 106531-84-4 3,4-Dimethyl-1-(6-methyl-benzothiazol-2-yl)-1H-pyrano[2,3-c]pyrazol-6-one 
• 104519-27-9 2-(4'-butyl-3',5'-dimethylpyrazol-1'-yl)-6-methylbenzothiazole 
• 131471-59-5 C₁₈H₂₃N₄PS 
• 109-89-7 diethylamine 
• 112518-02-2 6-(4-Methoxy-phenyl)-2-(6-methyl-benzothiazol-2-yl)-4,5-dihydro-2H-pyridazin-3-one 
• 131471-65-3 C₁₆H₂₆N₄O₂P₂S 
• 106515-46-2 1-(2'-benzothiazolyl)-3-methylpyrazol-5-ol 

Relevant academic research and scientific papers

The synthesis of some new 7-methyl-3-substituted-1,2,4-triazolo[3,4-b]benzothiazoles

New 7-Methyl-3-substituted-1,2,4-triazolo[3,4-b]benzothiazoles were synthesized from p-methylaniline to 5 with various aromatic carbonic acids. The yielded product 6a-j was investigated with Elemental analyses, NMR, MS and IR techniques.

Synthesis, crystal structure, and antioxidant property of a new Co(III) coordination polymer based on ligand (E)-2-{2-[1-(1-methyl-1H-benzo[d]imidazol-2-yl)ethylidene]hydrazinyl}benzo[d]thiazole

A new Co(III) complex, [CoL2](ClO4)(CH3CN) (1) (HL = (E)-2-{2-[1-(1-methyl-1H-benzo[d]imidazol-2-yl)ethylidene]hydrazinyl}benzo[d]thizole), has been prepared by solvent evaporation method, and characterized by single-crystal X-ray diffraction, bond valence sum, and elemental analysis. The result of single-crystal X-ray diffraction analysis indicates that each Co(III) ion is six-coordinated by six nitrogen atoms from two L- to form distorted octahedral geometry. The hydrogen bonds and π.π stacking interactions ensure the cohesion of crystal lattice in a 3D supramolecular framework in the solid state. The antioxidant activities of HL and 1 were also studied.

Microwave-assisted, solvent-free, one-pot, three-component synthesis of fused pyran derivatives containing benzothiazole nucleus catalyzed by pyrrolidine-acetic acid and their biological evaluation

Abstract: An efficient method for the synthesis of fused pyran derivatives has been developed by a one-pot, three-component, solvent-free reaction of 1H-pyrazole-4-carbaldehyde and various active methylenes and malononitriles under microwave irradiation in the presence of pyrrolidine-acetic acid as bifunctional catalyst. The salient features of this protocol are the solvent-free reaction, shorter reaction time, greater selectivity, and straightforward workup procedure. All the synthesized compounds were confirmed by analytical and spectral data. The synthesized compounds were investigated against a representative panel of pathogenic strains using the broth microdilution MIC method for their in vitro antimicrobial activity. Graphical abstract: [Figure not available: see fulltext.].

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.].

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Synthesis of 2-anilinopyridyl linked benzothiazole hydrazones as apoptosis inducing cytotoxic agents

A series of 2-anilinopyridyl linked benzothiazole-hydrazone conjugates (5a-aa) were designed, synthesized and evaluated for their in vitro cytotoxic potency against a panel of cancer cell lines like mouse skin melanoma (B16F10), lung adenocarcinoma (A549), breast adenocarcinoma (MCF-7), triple negative breast cancer (MDA-MB-231) and normal lung epithelial (L132) cell lines. Preliminary screening results revealed that some of these conjugates like 5i and 5l exhibited a significant antiproliferative effect against human breast cancer (MCF-7) with IC50 values of 1.03 and 1.69 μM respectively. Further, detailed biological studies of this promising conjugate (5i) were carried out on MCF-7 cells. The flow cytometric analysis revealed that this conjugate induces cell-cycle arrest in the G2/M phase in a dose dependent manner. Furthermore, in order to determine the effect of the conjugate on cell viability, various cell based assays such as clonogenic assay, ethidium bromide staining, Hoechst staining, detection of ROS generation and annexin V-FITC/PI assays were performed. In these studies, apoptotic features were clearly observed indicating that this conjugate inhibited cell proliferation by apoptosis.

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.

Design, synthesis, docking studies and biological evaluation of 2-phenyl-3-(Substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3H)-one derivatives as antimicrobial agents

Objective: A new series 2-phenyl-3-(substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3H)-one was prepared by the fusion method by reacting 2-phenyl benzoxazine with 2-hydrazino benzothiazole and it was evaluated for their antimicrobial activity against gram positive, gram negative bacteria and fungi. Methods: Titled compounds were synthesized by fusion reactions. These compounds were evaluated by in vitro antibacterial and antifungal activity using the minimum inhibitory concentration and zone of inhibition methods. The synthesized compounds were characterized with the help of infrared, NMR and mass spectral studies. The benzothiazole moiety and the quinazoline ring have previously shown DNA gyrase inhibition and target related antibacterial activity. Thus, molecular docking studies of synthesized compounds were carried out (PDB: 3G75) to study the possible interaction of compounds with the target. The batch grid docking was performed to determine the probable. Results: These compounds showed significant activity against gram positive and gram negative bacteria as well against the fungi. The compound A5 was found to be active against B. subtilis, P aeruginosa and C. albican at 12.5 μg/ml MIC. The compound A3 was found to be active against all microbial strains selected at 25 and 12.5 μg/ml MIC. Conclusion: Though the relationship between the activities shown by these compounds in, the antimicrobial study is still to be established, the docking studies conducted found to be consistent with antimicrobial results. Thus the results indicate that the designed structure can be a potential lead as an antimicrobial agent.

Regioselective Synthesis, Antimicrobial Evaluation and QSAR Studies of Some 3-Aryl-1-heteroarylindeno[1,2-c]pyrazol-4(1H)-ones

A series of seventeen 3-aryl-1-heteroarylindeno[1,2-c]pyrazol-4(1H)-ones (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 4p, 4q) has been synthesized and characterized by spectral (IR, 1H NMR, and mass), X-ray crystallography and analytical results. All the indenopyrazoles (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 4p, 4q) were tested for their in vitro antimicrobial activity against two Gram-positive bacteria viz. Bacillus subtilis (MTCC 441) and Staphylococcus aureus (MTCC 7443), two Gram-negative bacteria, viz. Escherichia coli (MTCC 42) and Pseudomonas aeruginosa (MTCC 741) and two fungi, viz. Candida albicans (MTCC 183) and Aspergillus niger (MTCC 282) using ceftriaxone and fluconazole as standard references against bacterial and fungal strains, respectively. Among the synthesized derivatives, 4f against B. subtilis and S. aureus, 4e against E. coli, 4g and 4j against P. aeruginosa, 4k and 4l against C. albicans, and 4k against A. niger were found to exhibit appreciable antimicrobial activities. However, 4g (minimum inhibitory concentration, 0.0036 μmol/mL) was found to be more potent than the reference, that is, fluconazole (minimum inhibitory concentration, 0.0050 μmol/mL) against A. niger. Moreover, both antibacterial and antifungal activities were found to be prolific. The radial distribution function parameters were found to be important for description of activities against the modeled strains in quantitative structure–activity relationship studies.