6973-51-9

Usage

Uses

Used in Dye Production:
4-nitrobenzothiazol-2-amine is utilized as an intermediate in the synthesis of various dyes. Its unique chemical structure allows for the creation of a wide array of colored compounds, making it a valuable component in the dye industry.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4-nitrobenzothiazol-2-amine serves as a key building block for the development of new drugs. Its reactivity and structural features enable the synthesis of diverse pharmaceutical compounds with potential therapeutic applications.
Used in Organic Synthesis:
4-nitrobenzothiazol-2-amine is employed as a reactant in various organic synthesis processes. Its strong electrophilic nature allows it to participate in multiple types of chemical reactions, contributing to the formation of complex organic molecules for different applications.

InChI:InChI=1/C7H5N3O2S/c8-7-9-6-4(10(11)12)2-1-3-5(6)13-7/h1-3H,(H2,8,9)

Upstream product

• 149-30-4 2-Mercaptobenzothiazole 
• 1280582-63-9 C₇H₅N₃O₂S 
• 88-74-4 2-nitro-aniline 
• 1147550-11-5 ammonium thiocyanate 
• 333-20-0 potassium thioacyanate 
• 2719-30-4 o-nitrophenylisothiocyanate 
• 51039-84-0 N-(2-nitrophenyl)thiourea 
• 95-16-9 1,3-Benzothiazole 
• 2942-08-7 4-nitrobenzothiazole 

Downstream Products

• 855283-00-0 2-chloro-benzothiazol-4-ylamine 
• 3507-30-0 2-chloro-4-nitrobenzothiazole 
• 934768-10-2 [1-(2,4-Dichloro-phenyl)-eth-(E)-ylidene]-(4-nitro-benzothiazol-2-yl)-amine 
• 80945-68-2 2-hydrazino-4-nitro-1,3-benzothiazole 
• 1280582-34-4 2,3-bis(4-methoxyphenyl)-5-nitroimidazo[2,1-b][1,3]benzothiazole 
• 1370409-56-5 2-(2-chlorophenyl)-3-(4-methylphenyl)-5-nitroimidazo[2,1-b][1,3]benzothiazole 
• 1370024-00-2 2-(2-chlorophenyl)-3-[4-(methylsulfanyl) phenyl]-5-nitroimidazo[2,1-b][1,3] benzothiazole 
• 1370024-90-0 2-(2,4-dichlorophenyl)-3-(4-methylphenyl)-5-nitroimidazo[2,1-b][1,3]benzothiazole 
• 1370409-57-6 2-(2,4-dichlorophenyl)-3-[4-(methylsulfanyl)phenyl]-5-nitroimidazo[2,1-b][1,3] benzothiazole 
• 1315085-61-0 C₂₁H₁₆N₁₀O₅S₃ 
• 1370445-77-4 C₁₅H₁₁N₃O₄S 
• 1370446-13-1 C₂₇H₂₀ClN₃O₄SSi 
• 1316270-47-9 C₂₀H₁₂N₈O₄S 
• 1268376-13-1 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-4-nitro-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole 

Relevant academic research and scientific papers

Small-compound enhancers for functional O-mannosylation of alpha-dystroglycan, and uses thereof

The present invention provides compounds that can enhance functional O-mannosylation of proteins including alpha-dystroglycan. Also provided are methods of preparation of the compounds defined by the formula I. Also provided are the methods of using the compounds or the pharmaceutical acceptable salts or prodrugs thereof in treating and preventing subjects suffering from the diseases including muscular dystrophies and cancers.

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.]

Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

Alpha-dystroglycan (α-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of α-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of α-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of α-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of α-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of α-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of α-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy.

A novel system for the synthesis of 2-aminobenzthiazoles using sodium dichloroiodate

2-Aminobenzthiazole is a privileged scaffold with a range of biological activities. However, to date, an efficient protocol for the synthesis of this ring system using aniline as a starting material has been lacking. Herein, for the first time, we describe a highly efficient and mild protocol for the synthesis of 2-aminiobenzthiazole using NaICl Georg Thieme Verlag Stuttgart ? New York.

Synthesis and antimicrobial activity of new pyridine derivatives-I

2-Amino substituted benzothiazoles 2a-l and 2-chloropyridine-3-carboxylic acid 3 were used to prepare 2-[N-(substitutedbenzothiazolyl)amino]pyridine-3- carboxylic acids (4a-l) in 2-ethoxy ethanol. Acid chlorides (5a-l) were condensed with 2-hydroxyethyl piperazine (6) and 2,3-dichloropiperazine (7) to prepare amide derivatives 2-[N-(substituted benzothiazolyl)amino]pyridin-3-yl (4-(2-hydroxyethyl)piperazin-1-yl)methanones (8a-l) and 2-[N-(substituted benzothiazolyl) amino]pyridin-3-yl(2,3- dichloropiperazine-1-yl)methanones (9a-l), respectively. The structures of new compounds have been established on the basis of elemental analysis and spectral (IR, 1H NMR, and Mass spectra) studies. The in vitro antimicrobial activity was screened for all the synthesized compounds. Variable and modest activity were observed against the investigated strains of bacteria and fungi. Springer Science+Business Media, LLC 2010.

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 preliminary in-vitro cytotoxic activity of novel substituted diaryl-imidazo [2, 1, b]-benzothiazole derivatives

A novel series of substituted diaryl imidazo[2, 1-b]benzothiazole derivatives (8a-y) were synthesized by condensation reaction between 2-amino benzothiazole derivatives (3a-g) and substituted a-bromo-1, 2-(substituted) diaryl-1-ethanones (7a-i). The structures of the synthesized compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopical data. The compounds (8a-y) were evaluated for their in-vitro cytotoxic activity on murine (B16F10) and human (MCF-7) cancer cells by using MTT assay. From the in vitro studies compounds 8p, 8u and 8y were found most effective with an IC50 range of 0.56-27.50 μM in MCF-7 and 2.57-36.54 μM in B16F10 cells.

Synthesis and preliminary in-vitro cytotoxic activity of novel substituted diaryl-imidazo [2,1,b]-benzothiazole derivatives

A novel series of substituted diaryl imidazo[2,1-b]benzothiazole derivatives (8a-y) were synthesized by condensation reaction between 2-amino benzothiazole derivatives (3a-g) and substituted α-bromo-1, 2-(substituted) diaryl-1-ethanones (7a-i). The structures of the synthesized compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopical data. The compounds (8a-y) were evaluated for their in-vitro cytotoxic activity on murine (B16F10) and human (MCF-7) cancer cells by using MTT assay. From the in vitro studies compounds 8p, 8u and 8y were found most effective with an IC50 range of 0.56-27.50 μM in MCF-7 and 2.57-36.54 μM in B16F10 cells.

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