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

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

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

Downstream Products

• 131471-67-5 C₁₅H₂₃ClN₄O₂P₂S 
• 109-89-7 diethylamine 
• 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 
• 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 
• 1316270-50-4 C₂₀H₁₂ClN₇O₂S 
• 1246493-48-0 3-(3-pyridyl)-5-(4-methylphenyl)-4-(N-(4-chloro-1,3-benzothiazol-2-yl)amino)-4H-1,2,4-triazole 
• 131471-60-8 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 BENZOTHIAZOLE DERIVATIVES WITH ENHANCED BIOLOGICAL ACTIVITY

The present invention discloses novel conjugates of benzothiazole derivatives with cystine and glucosamine and their method of synthesis. Their method of synthesis is easy and eco-friendly, avoiding the use of hazardous materials or reactions, The compounds offer technical advantages of increased solubility, potency, selectivity and biological activity. The novel compounds show antibacterial, antifungal and anticancer activities. Formula, physico-chemical data and biological activity of the novel derivatives are as given in Tables 1 to 9.

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.

AMINOMETHYLENE PYRAZOLONES WITH THERAPEUTIC ACTIVITY

A compound having the structure according to formula III wherein: X is NH or S;R1 is H or (1C-4C)alkyl;R2 is (1C-4C)alkyl, phenyl or a monocyclic aromatic ring having one or more N-, O-or S-atoms in the ring, which alkyl, phenyl or aromatic ring is optionally substituted with one or more groups selected from (1C-4C)alkyl, (1C-4C)alkyloxy, halo(1C-4C)alkyl, halo(1C-4C)alkyloxy, phenyloxy, phenylthio, halogen, or nitro;R3 and R4 are each independently H, (1C-6C)alkyl, (2C-6C) alkenyl, (2C-6C)alkynyl, cyano, (3C-6C)cycloalkyl, phenyl, a monocyclic aromatic ring having one or more N-, O- or S-atoms in the ring, a monocyclic non-aromatic ring having one or more N-, O- or S-atoms in the ring, each optionally substituted with hydroxyl, (1C-4C)alkoxy, phenyl, cycloalkyl, piperidyl, piperazinyl, furyl, thienyl, pirazinyl, pyrrolyl, 2H-pyrrolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyrrolidonyl, pyrrolinyl, imidazolinyl, imidazolyl, a monocyclic aromatic ring having one or more N-, O- or S- atoms in the ring, whereby each of these optional substituents is optionally further substituted with (1C-4C)alkyl, (1C-4C)alkyloxy, halo(1C-4C)alkyl, halo(1C-4C)alkyloxy, halogen, nitro or (1C-2C)dioxol forming a ring;or R3 and R4 form together pyrrolyl, imidazolyl, pyrazolyl, pyrrolidinyl, pyrrolinylimidazolidinyl, imidazolinyl, piperidyl, piperazinylmorpholinyl, each optionally substituted with (1C-6C)alkyl, phenyl(1C-4C)alkyl, phenylketo(1C-4C)alkyl; R5 is H, Cl, F, Br, Me, NO2, t-butyl, OCF3, OCH3, CF3; R6 is H, (1C-4C)alkyl, (1C-4C)alkyloxy, halo(1C-4C)alkyl, halo(1C-4C)alkyloxy, nitro or halogen;R7 is H,F, Cl, Br, Me, NO2, t-butyl, OCF3, OCH3, CF3; or pharmaceutically acceptable addition salts thereof for use in treatments of carcinoma, in particular to delay, prevent or reverse metastasis in prostate cancer.

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.

Synthesis and antibacterial evaluation of a novel series of 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazoles

The 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazole scaffold was selected as a central core structure for the discovery of novel antibacterial compounds. A systematic variation of the substituents on the oxo-pyrazole moiety, as well as on the benzo moiety, led to the creation of a small and focused library of benzothiazoles that was subjected to antibacterial screening. In a first round of screening, activity of the compounds against six representative microorganisms was established. For the most potent congeners, MIC values against S. aureus and P. aeruginosa were determined. The structure-activity relationship study clearly revealed that subtle structural variations influence the antibacterial activity to a large extent. The most potent congeners displayed MIC values of 3.30 μM.

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.

Antimycobacterial and antimicrobial study of new 1,2,4-triazoles with benzothiazoles

In this study, we report the antimycobacterial and antimicrobial evaluation of newly synthesized 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-substituted-1,3- benzothiazol-2-amino)-4H-1,2,4-triazole 6a-j in good yields. All the synthesized compounds have been established by elemental analysis, IR, 1H NMR, 13C-NMR and Mass spectral data. In-vitro antimycobacterial activity was carried out against (Mycobacterium tuberculosis) H37Rv strain using Lowenstein-Jensen medium and antimicrobial activity against two Gram positive bacteria (Staphylococcus aureus, Streptococcus pyogenes), two Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and three fungal species (Candida albicans, Aspergillus niger, Aspergillus clavatus) using the broth microdilution method. Compounds 2e, 6a, 6g, 6h, and 6j exhibited promising antimicrobial activity whereas compound 6j showed very good antimycobacterial activity. The antimycobacterial and antimicrobial evaluation of newly synthesized 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-substituted-1,3-benzothiazol- 2-amino)-4H-1,2,4-triazoles is reported in detail. Compounds 2e, 6a, 6g, 6h, and 6j exhibited promising antimicrobial activity whereas compound 6j showed very good antimycobacterial activity. Copyright

Exchange amination process for preparing 2-hydrazinobenzothiazoles

Improved process for the preparation of 2-hydrazinobenzothiazoles, comprising the reaction of corresponding 2-aminobenzothiazoles with hydrazine in the presence of acid, preferably in a selected solvent.