26278-79-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-benzothiazol-6-ol is used as a chemical intermediate for the synthesis of new benzothiazole derivatives. These derivatives exhibit anti-proliferative and anticonvulsant activities, making them valuable in the development of medications for the treatment of various diseases, including cancer and epilepsy.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Amino-benzothiazol-6-ol serves as a key building block for the creation of a wide range of benzothiazole-based compounds. These compounds can be further modified and functionalized to produce molecules with specific biological activities, such as pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
2-Amino-benzothiazol-6-ol is also utilized in research and development laboratories for the exploration of new chemical reactions and the synthesis of novel compounds. Its unique structure and reactivity make it an attractive candidate for studying various organic reactions and developing new synthetic methodologies.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 4103, 1970 DOI: 10.1021/jo00837a003

InChI:InChI=1/C7H6N2OS/c8-7-9-5-2-1-4(10)3-6(5)11-7/h1-3,10H,(H2,8,9)

Upstream product

• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 17356-08-0 thiourea 
• 106-51-4 p-benzoquinone 
• 94-45-1 2-Amino-6-ethoxybenzothiazole 
• 26278-78-4 2-amino-6-hydroxybenzothiazole hydrochloride salt 
• 1520-27-0 1-(4-hydroxyphenyl)thiourea 
• 51-78-5 p-aminophenol hydrochloride 
• 333-20-0 potassium thioacyanate 
• 123-30-8 4-amino-phenol 
• 1753-90-8 6-methoxy-1,2,3-benzothiadiazole 
• 13599-84-3 6-hydroxybenzothiazole 
• 3425-46-5 potassium selenocyanate 
• 312534-71-7 2-iodo-4-methoxyl-phenol 
• 54346-87-1 2-amino-5-methoxybenzothiazole 

Downstream Products

• 531557-00-3 3-(6-hydroxy-benzothiazol-2-ylamino)-1-phenylpropan-1-one 
• 875895-71-9 3,3'-dithiobis(4-aminophenol) 
• 934768-09-9 2-[1-(2,4-Dichloro-phenyl)-eth-(E)-ylideneamino]-benzothiazol-6-ol 
• 79890-34-9 2-(3-Hydroxy-phenyl)-benzo[d]imidazo[2,1-b]thiazol-7-ol 
• 79890-33-8 3-(7-Hydroxy-benzo[d]imidazo[2,1-b]thiazol-2-yl)-benzoic acid methyl ester 
• 945400-91-9 6-(tert-butyldimethylsilyloxy)benzo[d]thiazol-2-amine 
• 914224-34-3 2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazol-7-ol 
• 849235-69-4 4-[(6-hydroxy-benzothiazol-2-ylamino)-methyl]-benzoic acid methyl ester 
• 1309261-73-1 C₂₁H₁₄N₄O₂S 
• 1309261-60-6 3-(6-hydroxy-1,3-benzothiazol-2-yl)-2-phenylquinazolin-4(3H)-one 
• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 94-45-1 2-Amino-6-ethoxybenzothiazole 
• 14372-64-6 2-amino-6n-propoxy-benzothiazole 
• 14372-65-7 6-butoxy-benzothiazol-2-ylamine 

Relevant academic research and scientific papers

Pyrrolopyrrole aza-BODIPY near-infrared photosensitizer for dual-mode imaging-guided photothermal cancer therapy

A NIR photosensitizer pyrrolopyrrole aza-BODIPY (PPAB) was synthesized in a straightforward manner. Through the use of PPAB NPs as a photothermal agent, photoacoustic imaging (PAI) and NIR fluorescence imaging (NIR-FI) can be achieved in vivo. In addition, the photothermal ablation of tumor cells can be realized both in vitro and in vivo, even at a low concentration (0.5 mg kg?1).

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

An efficient one-pot synthesis of 2-aminobenzothiazoles from substituted anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H2O

Treatment of a variety of substituted anilines with benzyltrimethylammonium dichloroiodate (1.2 equiv) and ammonium thiocyanate (1.0 equiv) in DMSO:H2O (9:1) at 70 °C gave the corresponding 2-aminobenzothiazoles in excellent isolated yields (75–97%; ave. yield for all substrates = 90%). The reaction worked well for 2(4)-mono-, 2,4-di-, or 3,4,5-tri-substituted anilines, and a wide range of both electron donating groups (MeO, HO, CF3O, Me) and electron withdrawing groups (NO2, CN, CO2Et, CO2H, Cl, F) were well tolerated. This method provides a useful alternative to other methods that are either less efficient (requiring 3–7 fold equivalents of reagents) or utilize highly toxic and corrosive liquid Br2 as the oxidizing agent.

Benzo imidazo [2, 1-b] thiazole compound and application thereof (by machine translation)

The invention discloses a benzoimidazo [2, 1-b] thiazole compound and application thereof, and belongs to the technical field of medicines. The inhibitory activity of the synthesized benzimidazo [2, 1-b] thiazole analogues on FLTT3 is more than 90%, wherein the compounds (compounds 2 , 4, 6, 8 and 10) are IC of FLTT3-ITD kinase. 50 Lower value, in particular compound 2, IC IC50 The value is only 5.60 nm, and therefore the compound of the present invention may be used as an inhibitor FLTT3, or for preparing a drug capable of modulating or suppressing diseases associated with abnormal cell proliferation by affecting the enzymatic activity of one or more tyrosine kinases and interfering with aberrant cell proliferation, having a wide application prospect. (by machine translation)

Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Β-HSD10 with implications to Alzheimer’s disease treatment

Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymatic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurological diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approximately 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the phenyl ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC50 values of 1–2 μM and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.

Design, synthesis, and apoptosis-promoting effect evaluation of novel pyrazole with benzo[d]thiazole derivatives containing aminoguanidine units

New pyrazole with benzo[d]thiazoles containing hydrazinecarboximidamide substituent was synthesised and evaluated for cytotoxicity and apoptotic activity using the MTT assay, flow cytometry, and Western blot analysis. Among the compounds studied, (E)-2-((1-(6-((4-fluorobenzyl)oxy)benzo[d]thiazol-2-yl)-3-phenyl-1H- pyrazol-4-yl)methylene) hydrazinecarboximidamide (8l) was potent, with IC50 values of 2.41 μM, 2.23 μM, 3.75 μM and 2.31 μM in vitro anti-proliferative activity testing against triple-negative breast cancer cell line MDA-MB-231, non-triple-negative breast cancer MCF-7 cells, and human hepatocarcinoma HepG2 cells, and SMMC-7721 cells, respectively. Especially, the activity against MDA-MB-231 was similar to that of Doxorubicin, which was used as a positive control in this study. Next, the Annexin V/PI flow cytometry assay was used at different concentrations of compound 8l to demonstrate that compound 81 induced apoptosis of MDA-MB-231 cells in a concentration-dependent manner. Finally, these results were further verified by Western blot analysis. Taken together, the results of this study revealed that compound 8l may be a potential anticancer compound play a significant role in the subsequent researches.

Benzothiazole compound with anti-tumor activity and preparation method and application of compound

The invention discloses a benzothiazole compound with the anti-tumor activity and a preparation method and application of the compound and belongs to the technical field of anti-tumor medicine synthesis. The benzothiazole compound is characterized in that

Enhancement of Benzothiazoles as Pteridine Reductase-1 Inhibitors for the Treatment of Trypanosomatidic Infections

2-Amino-benzo[d]thiazole was identified as a new scaffold for the development of improved pteridine reductase-1 (PTR1) inhibitors and anti-trypanosomatidic agents. Molecular docking and crystallography guided the design and synthesis of 42 new benzothiazoles. The compounds were assessed for Trypanosoma brucei and Leishmania major PTR1 inhibition and in vitro activity against T. brucei and amastigote Leishmania infantum. We identified several 2-amino-benzo[d]thiazoles with improved enzymatic activity (TbPTR1 IC50 = 0.35 μM; LmPTR1 IC50 = 1.9 μM) and low μM antiparasitic activity against T. brucei. The ten most active compounds against TbPTR1 were able to potentiate the antiparasitic activity of methotrexate when evaluated in combination against T. brucei, with a potentiating index between 1.2 and 2.7. The compound library was profiled for early ADME toxicity, and 2-amino-N-benzylbenzo[d]thiazole-6-carboxamide (4c) was finally identified as a novel potent, safe, and selective anti-trypanocydal agent (EC50 = 7.0 μM). Formulation of 4c with hydroxypropyl-β-cyclodextrin yielded good oral bioavailability, encouraging progression to in vivo studies.

Synthesis, spectroscopic characterization, and computational studies of 2-cyano-6-hydroxybenzothiazole: A key synthetic intermediate of firefly luciferin

Firefly luciferin is widely applied as a biotechnological tool for visualizing various biological processes in vitro and in vivo. Chemically, 2-cyano-6-hydroxybenzothiazole, as a key synthetic intermediate of firefly luciferin, is obtained from 2-cyano-6-methoxybenzothiazole by changing the methoxy with a hydroxy group. However, this approach is costly and not suited for large-scale synthesis. Here we report cost-effective and efficient syntheses of 2-cyano-6-hydroxybenzothiazole through the catalytic Sandmeyer-type cyanation reaction. Our approach employs diazonium tetrafluoroborate salt of 2-amino-6-hydroxybenzothiazole as a cyanation substrate. The cyanation reaction proceeds efficiently under mild conditions by using Cu(I)/Cu(II)/N,N,N',N'-tetramethylethylenediamine as a catalyst. In addition, computational studies of the 2-cyano-6-hydroxybenzothiazole structure were performed based on the density functional theory method. The theoretical parameters of the optimized geometry were derived from the B3LYP/6-311 ++ G(d, p) method. Time-dependent density functional theory was applied to assign the electronic absorption bands observed experimentally and the1 H NMR chemical shifts were computed using the GIAO method. There was a significant relationship between computational studies and experimental results.

TYROSINE KINASE INHIBITOR AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

The present invention relates to a tyrosine kinase inhibitor and a pharmaceutical composition comprising same. The tyrosine kinase inhibitor of the present invention has the structures as shown in the following formula (I) or (II):