7471-03-6

Usage

Uses

Used in Dye and Pigment Production:
2-Amino-4-hydroxybenzothiazole is used as a key component in the production of dyes and pigments due to its chemical structure that facilitates color development and stability.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-Amino-4-hydroxybenzothiazole serves as a crucial intermediate in the synthesis of various drugs, contributing to the development of new medicinal compounds.
Used as an Intermediate in Organic Chemical Reactions:
2-Amino-4-hydroxybenzothiazole is utilized as an intermediate in a range of organic chemical reactions, playing a significant role in the synthesis of diverse chemical products. Its unique molecular structure allows for versatile applications in chemical processes.

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

Upstream product

• 5464-79-9 4-methoxy-1,3-benzothiazol-2-amine 
• 659731-49-4 acetic acid 2-acetylamino-benzothiazol-4-yl ester 
• 90180-68-0 4-methoxy-benzothiazol-2-ylamine hydrobromide 
• 51-78-5 p-aminophenol hydrochloride 
• 333-20-0 potassium thioacyanate 
• 95-55-6 2-amino-phenol 
• 1520-26-9 2-hydroxyphenylthiourea 

Downstream Products

• 19952-47-7 4-chlorobenzo[d]thiazol-2-amine 
• 659731-49-4 acetic acid 2-acetylamino-benzothiazol-4-yl ester 
• 862461-74-3 N-{4-[6-(4-trifluoromethyl-cyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide 
• 20600-52-6 N-(4-hydroxybenzo[d]thiazol-2-yl)acetamide 
• 659730-32-2 N-[4-[[6-[4-(trifluoromethyl)phenyl]-4-pyrimidinyl]oxy]-2-benzothiazolyl]acetamide 
• 879609-11-7 4-(2-chloro-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-amine 

Relevant academic research and scientific papers

Optimization and biological evaluation of 2-aminobenzothiazole derivatives as Aurora B kinase inhibitors

A strong relationship between abnormal functions of Aurora kinases and tumorigenesis has been reported for decades. Consequently, Aurora kinases serve as potential targets for anticancer agents. Here, we identified aminobenzothiazole derivatives as novel inhibitors of Aurora B kinase through bioisosteric replacement of the previous inhibitors, aminobenzoxazole derivatives. Most of the urea-linked aminobenzothiazole derivatives showed potent and selective inhibitory activity against Aurora B kinase over Aurora A kinase. Molecular modeling indicated that compound 15g bound well to the active site of Aurora B kinase and formed the essential hydrogen bonds. The potent compounds, 15g and 15k, were selected, and their biological effects were evaluated using HeLa cell lines. It was found that these compounds inhibited the phosphorylation of histone H3 at Ser10 and induced G2/M cell cycle arrest. We suggest that the reported compounds have the potential to be further developed as anticancer therapeutics.

Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules

DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.

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.

QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potent antibacterial agents

Present communication elicits the designing and synthesis of 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potential antibacterial agents. A number of substituted 2-amino benzothiazoles, 2-amino-5-[(E)-phenyl diazenyl] benzoic acid, and 2-phenyl-4H benzo[d] [1,3] oxazin-4-one were synthesized as the precursor substrates. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of IR, 1H NMR, Mass, and elemental analysis data. These compounds were screened in vitro for their antibacterial activity against a representative panel of Gram positive and Gram negative bacteria and models were generated through quantitative structure-activity relationship (QSAR).The activity contributions due to structural and substituent effects were determined using sequential regression procedure. The antimicrobial assay data show that the synthesized compounds are found to manifest profound antimicrobial activity. Springer Science+Business Media, LLC 2011.

Design, synthesis and activity of benzothiazole-based inhibitors of NO production in LPS-activated macrophages

Series of benzothiazoles were synthesized and evaluated their inhibitory activities for NO production in lipopolysaccharide-activated macrophages. The most potent compound was the indole-containing benzothiazole 3c with 4.18 μM of IC50. The mec

Practical synthesis of a vanilloid receptor-1 antagonist

(Chemical Equation Presented) Small molecule TRPV1 antagonists have been a recent focus in the search for pain treatment agents. We herein describe a practical and scalable synthesis of AMG 628 (1), a bis-substituted pyrimidine derivative that was identif

NOVEL COMPOUNDS

The invention provides compounds of formula (I) wherein m, R1, n, R2, q, X, Y, R3, R4, R5, R6, R7 and R8 are as defined in the specification, processes for their prepa

Combination of FBPase inhibitors and insulin sensitizers for the treatment of diabetes

Pharmaceutical compositions containing an FBPase inhibitor and an insulin sensitizer are provided as well as methods for treating diabetes and diseases responding to increased glycemic control, an improvement in insulin sensitivity, a reduction in insulin levels, or an enhancement of insulin secretion.

Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes

A combination therapy of at least one FBPase inhibitor and at least one other antidiabetic agent is disclosed.

Novel bisamidate phosphonate prodrugs

Novel bisamidate phosphonate prodrugs of FBPase inhibitors of the Formula IA: and their use in the treatment of diabetes and other conditions associated with elevated blood glucose.