51769-38-1

Basic information

• Product Name: 2(3H)-Benzothiazolone,4-chloro-,hydrazone(9CI)
• Synonyms: 2(3H)-Benzothiazolone,4-chloro-,hydrazone(9CI);(4-Chloro-benzothiazol-2-yl)-hydrazine;4-Chloro-2-hydrazinylbenzo[d]thiazole
• CAS NO: 51769-38-1
• Molecular Formula: C₇H₆ClN₃S
• Molecular Weight: 199.66
• Product Categories: BENZOTHIAZOLE
• Mol File: 51769-38-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(3H)-Benzothiazolone,4-chloro-,hydrazone(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Benzothiazolone,4-chloro-,hydrazone(9CI)(51769-38-1)
• EPA Substance Registry System: 2(3H)-Benzothiazolone,4-chloro-,hydrazone(9CI)(51769-38-1)

Safety Data

• Hazardous Substances Data: 51769-38-1(Hazardous Substances Data)

Usage

Molecular structure

Heterocyclic compound
The compound contains both benzene and thiazole rings, which are characterized by the presence of heteroatoms (atoms other than carbon) in their structures.

Chloro group

Presence of chlorine atom
The chloro group (-Cl) indicates that one of the hydrogen atoms in the benzene ring is replaced by a chlorine atom, making the compound more reactive and affecting its properties.

Hydrazone derivative

Functional group containing nitrogen and hydrogen atoms
The hydrazone group (-NHNH2) is a functional group consisting of a nitrogen atom double-bonded to two hydrogen atoms and bonded to a carbonyl group (C=O). This group is known for its reactivity in various chemical reactions.

Potential applications

Organic synthesis, chemical reactions, and pharmaceutical research
Due to its unique structure and reactivity, 2(3H)-Benzothiazolone,4-chloro-,hydrazone(9CI) may be used in the synthesis of other compounds, as a reactant in chemical reactions, or as a starting material for pharmaceutical research and drug development.

Upstream product

• 95-51-2 o-chloroaniline 
• 5344-82-1 o-chlorophenylthiourea 
• 608-31-1 2,6-Dichloroaniline 
• 3507-40-2 4-chloro-2-(methylsulfanyl)benzo[d]thiazole 
• 1849-65-6 4-chloro-2-mercaptobenzothiazole 
• 3622-30-8 2,4-dichlorobenzo[d]thiazole 
• 19952-47-7 4-chlorobenzo[d]thiazol-2-amine 

Downstream Products

• 131471-66-4 C₁₁H₁₅ClN₄O₂P₂S 
• 124-40-3 dimethyl amine 
• 1268376-15-3 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-4-chloro-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole 
• 1316270-50-4 C₂₀H₁₂ClN₇O₂S 
• 1452793-01-9 4-[1-aminomethylidene]-2-(4-chlorobenzothiazol-2-yl)-5-phenyl-2,4-dihydropyrazol-3-one 
• 1452793-06-4 2-(4-chlorobenzothiazol-2-yl)-4-[1-dimethylaminomethylidene]-5-phenyl-2,4-dihydropyrazol-3-one 
• 1452793-04-2 2-(4-chlorobenzothiazol-2-yl)-5-phenyl-1,2-dihydropyrazol-3-one 
• 1246493-48-0 3-(3-pyridyl)-5-(4-methylphenyl)-4-(N-(4-chloro-1,3-benzothiazol-2-yl)amino)-4H-1,2,4-triazole 
• 131471-67-5 C₁₅H₂₃ClN₄O₂P₂S 
• 109-89-7 diethylamine 
• 131471-60-8 C₁₇H₂₀ClN₄PS 

Relevant articles and documents

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.

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 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.