20174-70-3

Usage

Uses

Used in Pharmaceutical Industry:
2-HYDRAZINO-6-METHOXY-1,3-BENZOTHIAZOLE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and functional groups contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-HYDRAZINO-6-METHOXY-1,3-BENZOTHIAZOLE serves as a crucial component in the production of agrochemicals. Its incorporation aids in the creation of effective pesticides and other agricultural chemicals that enhance crop protection and yield.
Used in Dye Industry:
2-HYDRAZINO-6-METHOXY-1,3-BENZOTHIAZOLE is utilized as a building block in the synthesis of dyes. Its chemical properties allow for the development of dyes with specific color characteristics and improved performance in various applications.
Used in Material Science:
In the field of material science, 2-HYDRAZINO-6-METHOXY-1,3-BENZOTHIAZOLE is employed for its potential applications in the development of new materials with unique properties. Its presence in these materials can enhance their performance and contribute to advances in various industries.
Used in Biomedical Research:
2-HYDRAZINO-6-METHOXY-1,3-BENZOTHIAZOLE is also recognized for its potential use in biomedical research. Its biological activities and chemical properties make it a promising candidate for the study of new therapeutic agents and diagnostic tools.

InChI:InChI=1/C8H9N3OS/c1-12-5-2-3-6-7(4-5)13-8(10-6)11-9/h2-4H,9H2,1H3,(H,10,11)

Upstream product

• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 104-94-9 4-methoxy-aniline 
• 2605-14-3 2-chloro-6-(methyloxy)-1,3-benzothiazole 
• 26278-79-5 2-amino-6-hydroxybenzothiazole 
• 14372-55-5 1-Methoxy-3-rhodan-4-amino-benzol 
• 2293-07-4 1-(4-methoxyphenyl)thiourea 

Downstream Products

• 106515-43-9 1-(6-Methoxy-benzothiazol-2-yl)-3,4-dimethyl-1H-pyrano[2,3-c]pyrazol-6-one 
• 78364-38-2 2-(4-Ethyl-3,5-dimethyl-pyrazol-1-yl)-6-methoxy-benzothiazole 
• 75307-13-0 6-methoxy-2-(3',5'-dimethylpyrazol-1'-yl)benzothiazole 
• 112445-61-1 2-(6-Methoxy-benzothiazol-2-yl)-6-(4-methoxy-phenyl)-4,5-dihydro-2H-pyridazin-3-one 
• 153708-66-8 5-(4-Chlorophenyl)-3-(3-hydroxypropyl)-1-(6-methoxy-2-benzothiazolyl)pyrazole 
• 1111097-35-8 C₁₅H₁₃ClN₄OS₂ 
• 1111097-29-0 C₁₅H₁₃FN₄OS₂ 
• 1111097-32-5 C₁₅H₁₃BrN₄OS₂ 
• 1246493-43-5 3-(3-pyridyl)-5-(4-methylphenyl)-4-(N-(6-methoxy-1,3-benzothiazol-2-yl)amino)-4H-1,2,4-triazole 

Relevant academic research and scientific papers

Synthesis and study on magnetic resonance imaging performance of Gd(III)-DTPA-bisbenzothiazol hydrazide

In this paper, 2-hydrazino-6-methoxy-1,3-benzothiazole was introduced into diethylenetriamine pentaacetic ( DTPA) by acylation reaction. The corresponding non-ion Gd(III) complex holding promise of a single molecule magnetic resonance imaging (MRI) contrast agent was obtained by treating this ligand with GdCl3·6H2 O. The efficacy of the contrast agent was assessed by measuring the longitudinal relaxivity (r1), the r1 of Gd(III)-DTPA-bisbenzothiazole hydrazide was up to 6.44 mM-1·s-1, which was 1.8 times higher than that of the analogous MRI contrast agent Gd(III)-DTPA(r1 = 3.64 mM-1·s-1 ) in commercial use. In addition, in vitro MR images on a 0.5 T magnetic field exhibited a remarkable enhancement of signal contrast for Gd(III)-DTPA-bisbenzothiazole hydrazide than Gd(III)-DTPA. These results demonstrate that this non-ion Gd(III) complex acts as a potentially MRI contrast agent.

Design, synthesis, characterization and biological evaluation of 6- methoxy-2-aminobenzothioate derivatives against certain bacterial strains

The current work reports the synthesized and biological evaluation of 6-methoxy-2-amino benzothiazole (A1), which was prepared via reaction p-Ansidine with ammonium thiocyanate followed by the oxidative ring closure of the resultant thiourea with a catalytic amount of bromine, in the alkaline medium. The resulting compound(A1) underwent condensation reactions with various kinds of aldehydes to produce Hydrazones (A3ad). 6-methoxy2-hydrazinobenzothiazole (A2) was prepared through the reaction of the compound (A1) with 99.9 % hydrazine hydrate in the presence of concentrated HCl and ethylene glycol solution. After that, the compound (A2) was reacted with ethyl acetoacetate in alcohol to yield corresponding pyrazole-6- methoxybenzothiazole (A4). Moreover, the compound (A2) was reacted with 4- substituted aromatic aldehydes in absolute ethanol to create Hydrazones (A5a-d). Synthesized compounds were investigated as anti-bacterial activity against five microorganisms: (Gram-positive: Bacillus subtilis & Staphylococcus aurea). (Gramnegative: Pseudomonas aeruginous Escherichia coli and Enterobacter)

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.].

Design, synthesis, and apoptosis-promoting effect evaluation of novel pyrazole with benzo[d]thiazole derivatives containing aminoguanidine units

New pyrazole with benzo[d]thiazoles containing hydrazinecarboximidamide substituent was synthesised and evaluated for cytotoxicity and apoptotic activity using the MTT assay, flow cytometry, and Western blot analysis. Among the compounds studied, (E)-2-((1-(6-((4-fluorobenzyl)oxy)benzo[d]thiazol-2-yl)-3-phenyl-1H- pyrazol-4-yl)methylene) hydrazinecarboximidamide (8l) was potent, with IC50 values of 2.41 μM, 2.23 μM, 3.75 μM and 2.31 μM in vitro anti-proliferative activity testing against triple-negative breast cancer cell line MDA-MB-231, non-triple-negative breast cancer MCF-7 cells, and human hepatocarcinoma HepG2 cells, and SMMC-7721 cells, respectively. Especially, the activity against MDA-MB-231 was similar to that of Doxorubicin, which was used as a positive control in this study. Next, the Annexin V/PI flow cytometry assay was used at different concentrations of compound 8l to demonstrate that compound 81 induced apoptosis of MDA-MB-231 cells in a concentration-dependent manner. Finally, these results were further verified by Western blot analysis. Taken together, the results of this study revealed that compound 8l may be a potential anticancer compound play a significant role in the subsequent researches.

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.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

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

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.

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.