20174-72-5

Basic information

• Product Name: 2(3H)-Benzothiazolone,5-chloro-,hydrazone(9CI)
• Synonyms: 2(3H)-Benzothiazolone,5-chloro-,hydrazone(9CI);5-chloro-2-hydrazinylbenzo[d]thiazole
• CAS NO: 20174-72-5
• Molecular Formula: C₇H₆ClN₃S
• Molecular Weight: 199.66
• Product Categories: BENZOTHIAZOLE
• Mol File: 20174-72-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(3H)-Benzothiazolone,5-chloro-,hydrazone(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Benzothiazolone,5-chloro-,hydrazone(9CI)(20174-72-5)
• EPA Substance Registry System: 2(3H)-Benzothiazolone,5-chloro-,hydrazone(9CI)(20174-72-5)

Safety Data

• Hazardous Substances Data: 20174-72-5(Hazardous Substances Data)

Usage

Structure

2(3H)-Benzothiazolone derivative with a hydrazone group

Type

Heterocyclic compound

Chloro derivative

Contains a chlorine atom

Potential uses

Schiff base formations, condensation reactions with carbonyl compounds, pharmaceuticals, agrochemicals, and new material development

Additional research needed

To fully understand properties and potential uses.

Upstream product

• 95-82-9 2,5 dichloroaniline 
• 20358-00-3 2-amino-5-chlorobenzothiazole 
• 108-42-9 3-chloro-aniline 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 5331-91-9 5-chloro-2-mercaptobenzothiazole 
• 29203-75-6 5-chloro-2-(methylsulfonyl)benzothiazole 
• 3507-41-3 5-Chloro-2-(methylthio)benzothiazole 
• 4947-89-1 1-(3-chlorophenyl)-2-thiourea 

Downstream Products

• 1354964-53-6 C₁₆H₁₁ClN₄O₄S 
• 1452793-08-6 4-[1-aminomethylidene]-2-(5-chlorobenzothiazol-2-yl)-5-phenyl-2,4-dihydropyrazol-3-one 
• 1452793-11-1 2-(5-chlorobenzothiazol-2-yl)-4-[1-dimethylaminomethylidene]-5-phenyl-2,4-dihydropyrazol-3-one 
• 1279099-66-9 2-(5-chlorobenzothiazol-2-yl)-1,2-dihydro-5-phenyl-3H-pyrazol-3-one 
• 1374820-28-6 C₁₇H₁₆Cl₃N₃S 
• 2941-48-2 2,5-Dichloro-benzothiazole 

Relevant articles and documents

Synthesis, p38α MAP kinase inhibition, anti-inflammatory activity, and molecular docking studies of 1,2,4-triazole-based benzothiazole-2-amines

Recent studies have demonstrated that inhibition of p38α MAP kinase could effectively inhibit pro-inflammatory cytokines including TNF-α and interleukins. Thus, inhibition of this enzyme can prove greatly beneficial in the therapy of chronic inflammatory diseases. A new series of N-[3-(substituted-4H-1,2,4-triazol-4-yl)]-benzo[d]thiazol-2-amines (4a–n) were synthesized and subjected to in vitro evaluation for anti-inflammatory activity (BSA anti-denaturation assay) and p38α MAPK inhibition. Among the compounds selected for in vivo screening of anti-inflammatory activity (4b, 4c, 4f, 4g, 4j, 4m, and 4n), compound 4f was found to be the most active with an in vivo anti-inflammatory efficacy of 85.31% when compared to diclofenac sodium (83.68%). It was also found to have a low ulcerogenic risk and a protective effect on lipid peroxidation. The p38α MAP kinase inhibition of this compound (IC50 = 0.036 ± 0.12 μM) was also found to be superior to the standard SB203580 (IC50 = 0.043 ± 0.27 μM). Furthermore, the in silico binding mode of the compound on docking against p38α MAP kinase exemplified stronger interactions than those of SB203580.

COMPOUNDS AND METHODS FOR TREATING CANCER

Substituted hydrazone compounds, methods of making such compounds and metal complexes thereof, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds and metal complexes to treat, prevent or ameliorate cancer are provided.

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.