19952-47-7

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4-CHLOROBENZOTHIAZOLE is used as an antiviral agent for its in vivo effects against various influenza A2 strains. It serves as a promising compound in the development of antiviral medications to combat influenza and potentially other viral infections.
Used in Research and Development:
In the field of research and development, 2-AMINO-4-CHLOROBENZOTHIAZOLE is utilized as a key compound for studying its antiviral properties and potential applications in the creation of new antiviral drugs. Its chemical structure and properties make it an interesting candidate for further investigation and development in the pharmaceutical sector.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A halogenated amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 2-AMINO-4-CHLOROBENZOTHIAZOLE emits very toxic fumes of chloride ion, SOx and NOx.

Fire Hazard

Flash point data for 2-AMINO-4-CHLOROBENZOTHIAZOLE are not available; however, 2-AMINO-4-CHLOROBENZOTHIAZOLE is probably combustible.

InChI:InChI=1/C7H5ClN2S/c8-4-2-1-3-5-6(4)10-7(9)11-5/h1-3H,(H2,9,10)

Upstream product

• 5344-82-1 o-chlorophenylthiourea 
• 89642-58-0 2-azido-4-chloro-benzothiazole 
• 10025-67-9 disulfur dichloride 
• 333-20-0 potassium thioacyanate 
• 95-51-2 o-chloroaniline 
• 1147550-11-5 ammonium thiocyanate 
• 3048-45-1 4-chloro-1,3-benzothiazole 
• 3425-46-5 potassium selenocyanate 
• 21258-05-9 N-benzoyl-N'-(2-chlorophenyl)thiourea 
• 4947-89-1 1-(3-chlorophenyl)-2-thiourea 
• 27058-83-9 BrH*C₇H₅ClN₂S 
• 137-04-2 2-chloroaniline hydrochloride 
• 7471-03-6 2-amino-4-hydroxybenzothiazole 
• 109-86-4 2-methoxy-ethanol 

Downstream Products

• 103030-22-4 2-bromo-propionic acid-(4-chloro-benzothiazol-2-ylamide) 
• 100856-54-0 N-(4-chloro-benzothiazol-2-yl)-benzamide 
• 70705-46-3 ethyl 5-chloroimidazo<2,1-b>benzothiazole-2-carboxylate 
• 63205-30-1 3-benzyl-2-(4-chloro-benzothiazol-2-ylimino)-5-methyl-thiazolidin-4-one 
• 3622-30-8 2,4-dichlorobenzo[d]thiazole 
• 1457-46-1 3-phenylrhodanine 
• 117844-39-0 N,N'-Bis-(4-chloro-benzothiazol-2-yl)-hydrazine; hydrobromide 
• 77203-68-0 2,4-Dibromo-6-{[(E)-4-chloro-benzothiazol-2-ylimino]-methyl}-phenol 
• 78417-52-4 3,5-Dibromo-N-(4-chloro-benzothiazol-2-yl)-2-hydroxy-benzamide 
• 77414-54-1 N-(4-chlorobenzothiazol-2-yl)cyclopropanecarboxamide 
• 104497-69-0 2-(4-Chlorobenzothiazolyl)hydrazonobutyl-1-aminophenyl-1,3-dione 
• 77203-64-6 4-Bromo-2-{[(E)-4-chloro-benzothiazol-2-ylimino]-methyl}-phenol 
• 51769-38-1 (4-chloro-1,3-benzothiazol-2-yl)hydrazine 
• 3048-45-1 4-chloro-1,3-benzothiazole 

Relevant academic research and scientific papers

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

Self-assembly of a benzothiazolone conjugate into panchromatic fluorescent fibres and their application in cellular imaging

We report the synthesis and characterization of the structures formed by self-assembly of 4-chloro-2(3H)-benzothiazolone (CBT) into panchromatic fibres and their application in cellular imaging. The aggregation properties of the synthesized compound were studied extensively under different solvents and concentrations and their morphologies examined at a supramolecular level by various microscopic techniques such as atomic force microscopy (AFM), fluorescence microscopy, and optical microscopy. Interestingly, the self-assembled structures formed byCBTreveal panchromatic emission properties and show blue, green, and red fluorescence under different excitation wavelengths. The mechanism of structure formation of the self-assemblies was studied through different techniques such as concentration-dependent1H-NMR, ATR-FTIR, UV-visible spectroscopy, and fluorescence spectroscopy. Finally, the utility ofCBTfor cell imaging applications was demonstrated and it can be noted thatCBTwas efficiently taken up by mammalian cells and the cells revealed panchromatic emission in the blue, green, and red channels. The intensities of the fluorescence observed were blue > green > red and the dye interestingly does not exhibit any fluorescence quenching.

SN-Donor methylthioanilines and copper(II) complexes: Synthesis, spectral properties, and in vitro antimicrobial activity

Methylthioanilines, a series of sulfur-nitrogen donor ligands substituted with OCH3, CH3, Cl, and Br, and their copper(II) complexes have been synthesized and characterized by 1H and 13C NMR, elemental analysis, FTIR, UV-Vis and EPR spectra, molar conductance, and magnetic susceptibility measurements. The NMR spectra of the ligands revealed that the para/ortho protons and para carbon were sensitive to the electronic effect of substituents. The CHNS analysis presented CuLCl2 (L = OCH3, CH3, Cl) and CuL2Cl2 (L = Br) stoichiometries for the copper complexes. FTIR spectra showed that the bidentate ligands were coordinated to the copper ion through their nitrogen and sulfur atoms. The electronic spectra have suggested square planar and octahedral geometries for these complexes. The EPR spectra demonstrated that the solid state copper(II) complexes possess dx2-y2 orbital ground state and g= > g > 2.0023 in a tetragonal environment. The compounds were evaluated for in vitro antimicrobial activity against S. aureus, B. subtilis, E. coli, and C. albicans. The copper complexes showed higher activity than the parent ligands against S. aureus and B. subtilis; the electron-donating OCH3 and CH3 derivatives were more active than the withdrawing Br- A nd Cl-substituted compounds.

Discovery of 18β-glycyrrhetinic acid conjugated aminobenzothiazole derivatives as Hsp90-Cdc37 interaction disruptors that inhibit cell migration and reverse drug resistance

A series of 18β-glycyrrhetinic acid (GA) conjugated aminobenzothiazole derivatives were designed, synthesized and evaluated for disruption activity of Hsp90-Cdc37 as well as the effects of in vitro cell migration. These compounds exhibited relatively good disruption activity against Hsp90-Cdc37 with IC50 values in low micromolar range. A docking study of the most active compound 11g revealed key interactions between 11g and Hsp90-Cdc37 complex in which the benzothiazole moiety and the amine chain group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU and showed potent suppression activity against drug-resistant cancer cells. In particular, compound 11 g appeared to be the most potent compound against the A549 cell line, at least partly, by inhibition of the activity of Hsp90 and apoptosis induction. The treatment of A549 cells with compound 11g resulted in inhibition of in vitro cell migration through wound healing assay and S phase of cell cycle arrested. In addition, 11g-induced apoptosis was significantly facilitated in A549 cells. Thus, we conclude that GA aminobenzothiazole derivatives may be the potential Hsp90-Cdc37 disruptors with the ability to suppress cells migration and reversed drug-resistant.

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.

Compounds for treating spinal muscular atrophy

Provided herein are compounds, compositions thereof and uses therewith for treating spinal muscular atrophy. In a specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN2 into mRNA that is transcribed from the SMN2 gene. In another specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 into mRNA that is transcribed from the SMN1 gene. In yet another embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 and SMN2 into mRNA that is transcribed from the SMN1 and SMN2 genes, respectively.

Efficient and facile protocol for one-pot synthesis of 2-amino-substituted benzothiazoles catalyzed by nano-BF3/SiO2 under mild conditions

Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles through the reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described. In this method, all of the 2-amino-substituted benzothiazoles were obtained in high to excellent yields and short reaction times under mild conditions. The structures of the resulting products were characterized and confirmed by melting point, FT-IR, 1H NMR and 13C NMR techniques. Graphical Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles by reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described.[Figure not available: see fulltext.]

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, cytotoxic evaluation, and in silico studies of substituted N-alkylbromo-benzothiazoles

In efforts to develop a new class of anticancer agents with improved efficacy and selective action, a series of N-alkylbromo-benzothiazoles were synthesized and evaluated for in vitro cytotoxic activity against various human cancer cell lines such as lung (A-549), prostate (PC-3), leukemia (THP-1), and colon (Caco-2). They were found to be highly active against prostate (PC-3) and leukemia (THP-1) cancer cells, moderately active against colon (Caco-2) cancer cells and less active against lung (A-549) cancer cells. Of the 12 compounds, two (11d, 11j) exhibit IC50 values of ≤ 1 μM against leukemia (THP-1) cancer cell lines. Compound 11l showed significant cytotoxic activity against the PC-3 (IC50 = 0.6 μM), THP-1 (IC50 = 3 μM) and Caco-2 cell lines (IC50 = 9.9 μM), respectively. Docking study of the synthesized ligand was done on epidermal growth factor receptor using ArgusLab flexible docking, to determine their observed activity. Further QSAR investigations with stepwise multiple linear regression analysis were applied to find correlation between various physicochemical parameters and anticancer activity. The QSAR results showed that anticancer activity could be modeled with descriptors. The predictive ability of models was cross-validated by observation of the low residual activity values and adjusted coefficient of variation (radj2) obtained by leave-one-out technique.

Design, synthesis and anticonvulsant evaluation of N-(benzo[d]thiazol-2- ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)-carbothioamide derivatives: A hybrid pharmacophore approach

Novel N-(benzo[d]thiazol-2-ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)- carbothioamide derivatives were synthesized and evaluation of their anticonvulsant effects was done using various models of experimental epilepsy. Initial anticonvulsant activities of the compounds were investigated using intraperitoneal (i.p.) maximal electroshock shock (MES), subcutaneous pentylenetetrazole (scPTZ) seizure models in mice. The quantitative assessment after oral administration in rats showed that the most active was 2-methyl-4-oxo-N-(6-(trifluoromethoxy)benzo[d]thiazol-2-ylcarbamoyl) quinazoline-3(4H)-carbothioamide (SA 24) with ED50 values of 82.5 μmol/kg (MES) and 510.5 μmol/kg (scPTZ). This molecule was more potent than phenytoin and ethosuximide which were used as reference antiepileptic drugs. To explain the possible mechanism for anticonvulsant action, some of the selected active compounds were subjected to GABA (γ-amino butyric acid) assay and AMPA ((S)-2-amino-3-(3-hydroxyl-5-methyl-4-isoxazolyl) propionic acid) induced seizure test.