20358-07-0

Usage

Uses

Used in Organic Chemical Synthesis:
2-AMINO-5-FLUOROBENZOTHIAZOLE is used as an organic chemical synthesis intermediate for [application reason]. Its distinct chemical properties allow it to be a key component in the creation of various organic compounds, contributing to the development of new materials and substances with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-AMINO-5-FLUOROBENZOTHIAZOLE is used as a building block for the development of new drugs. Its unique structure can be utilized to create novel drug candidates with potential therapeutic applications, such as those targeting specific diseases or conditions.
Used in Chemical Research:
2-AMINO-5-FLUOROBENZOTHIAZOLE is also used in chemical research as a model compound to study various chemical reactions and mechanisms. Its distinct properties make it an ideal candidate for understanding the behavior of similar compounds and for developing new synthetic methods and techniques.
Used in Material Science:
In the field of material science, 2-AMINO-5-FLUOROBENZOTHIAZOLE can be used as a component in the development of new materials with specific properties. Its unique molecular structure can contribute to the creation of materials with enhanced performance characteristics, such as improved stability, reactivity, or selectivity.
Overall, 2-AMINO-5-FLUOROBENZOTHIAZOLE is a versatile compound with a wide range of applications across various industries, including pharmaceuticals, chemical research, and material science. Its unique properties make it a valuable asset in the development of new products and technologies.

InChI:InChI=1/C7H5FN2S/c8-4-1-2-6-5(3-4)10-7(9)11-6/h1-3H,(H2,9,10)

Upstream product

• 458-05-9 1-(3-fluorophenyl)thiourea 
• 21325-03-1 4-fluoro-2-nitro-1-thiocyanato-benzene 
• 371-42-6 4-Fluorothiophenol 
• 825-83-2 4-trifluoromethylbenzenethiol 
• 372-19-0 meta-fluoroaniline 
• 333-20-0 potassium thioacyanate 
• 364-78-3 2-nitro-4-fluoroaniline 
• 82635-62-9 1-benzoyl-3-(3-flourophenyl)thiourea 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 224791-45-1 4,4'-difluoro-2,2'-diaminodiphenyl disulfide 
• 154327-27-2 2-chloro-5-fluoro-1,3-benzothiazole 
• 441715-01-1 2-bromo-5-fluoro-1,3-benzothiazole 
• 131105-89-0 2-amino-4-fluorobenzene-1-thiol 
• 1374820-30-0 C₁₇H₁₆Cl₂FN₃S 
• 441715-05-5 [5-chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl]acetic acid ethyl ester 
• 441715-07-7 C₂₈H₂₉ClF₃N₃O₄S 
• 441715-04-4 C₂₈H₃₀ClF₂N₃O₄S 
• 441712-36-3 trans-4-[1-[[5-chloro-2-fluoro-4-(5-fluoro-2-benzothiazolyl)aminophenyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 441712-35-2 trans-4-[1-[[3-chloro-4-(5-fluoro-2-benzothiazolyl)aminophenyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 293316-38-8 (2-amino-4-fluorophenylsulfanyl)acetonitrile 
• 63755-07-7 bis(2-amino-5-fluorophenyl)disulfide 
• 293316-40-2 N-(2-cyanomethylsulfonyl-5-fluorophenyl)acetamide 
• 293316-39-9 N-(2-cyanomethylsulfanyl-5-fluorophenyl)acetamide 

Relevant academic research and scientific papers

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

ANTIBIOTIC COMPOUNDS, PHARMACEUTICAL FORMULATIONS THEREOF AND METHODS AND USES THEREFOR

The present invention relates to compounds of formula (I) wherein G1 to G8 are as defined herein. The compounds are PK inhibitors and as such represent a new approach to treating pathogenic infections, including multidrug resistant pathogens. Disclosed herein are the compounds of formula (I), pharmaceutical compositions comprising the compounds of formula (I) and their use in the treatment of antimicrobial infection. (Formula (1))

PHARMACEUTICAL COMPOSITION FOR TREATING OR PREVENTING FOOT-AND-MOUTH DISEASE

The present invention refers to benzothiazole derivatives and its pharmaceutically acceptable salt as active ingredients opening including inverse number relates to a pharmaceutical composition for treating or preventing is. In addition, opening the present invention refers to treatment or prevention of inverse number relates to method. (by machine translation)

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.

Electrochemical intramolecular c-h amination: Synthesis of benzoxazoles and benzothiazoles

A new method for metal-free intramolecular C-H amination has been developed. Electrochemical oxidation of 2-pyrimidyloxybenzenes and 2-pyrimidylthiobenzenes, which can be easily prepared from phenols and thiophenols, respectively, followed by the treatment of the resulting pyrimidinium ions with piperidine gives 2-aminobenzoxazoles and 2-aminobenzothiazoles, respectively.

IMIDAZOTHIADIAZOLE DERIVATIVES AS PROTEASE ACTIVATED RECEPTOR 4 (PAR4) INHIBITORS FOR TREATING PLATELET AGGREGATION

The present invention provides imidazothiadiazole compounds of Formula (I) wherein A, B, D, Rx, R1, R2, R3, X1, X2 and s are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt or solvate form thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of platelet aggregation and thus can be used as medicaments.

Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics.

Synthesis of carbon-11 labeled fluorinated 2-arylbenzothiazoles as novel potential PET cancer imaging agents

Fluorinated 2-arylbenzothiazoles are new potential antitumor drugs, which show potent and selective inhibitory activity against breast, lung, and colon cancer cell lines. Carbon-11 labeled fluorinated 2-arylbenzothiazoles may serve as novel probes for positron emission tomography (PET) to image tyrosine kinase in cancers. The preparation of 4-fluorinated 2-arylbenzothiazoles 4-fluoro-2-(3-benzloxy-4-methoxyphenyl)benzothiazole (6a) and 4-fluoro-2-(3,4-dimethoxyphenyl)benzothiazole (6b) was achieved by a modification of Jacobson thioanilide radical cyclization chemistry. Hydrogenolytic cleavage of the benzyl ether group of compound 6a using H2/Pd-C provided the precursor 4-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole (7) for radiolabeling. Synthesis of radiolabeling precursors and the reference standards 5- and 6-fluorinated arylbenzothiazoles (11c-n) was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. The target radiotracers carbon-11 labeled 4-, 5-, and 6-fluorinated arylbenzothiazoles (3-[11C]6b, 4-[11C]11c, 3-[11C]11c, 5-[11C]11f, 4-[11C]11f, 4-[11C]11i, 3-[11C]11i, 5-[11C]11l, and 4-[11C]11l) were prepared by O-[11C]methylation of the phenolic hydroxyl precursors (7, 11d, 11e, 11g, 11h, 11j, 11k, 11m, and 11n) with [11C]methyl triflate and isolated by solid-phase extraction (SPE) purification in 30-55% radiochemical yields.

Novel 1,4-benzothiazephine and 1,5-benzothiazepine compounds as inhibitors of apical sodium co-dependent bile acid transport and taurocholate uptake

Compounds, pharmaceutical compositions, and methods for the treatment of a hyperlipidemic condition in a subject. The compounds of the present invention are apical sodium co-dependent bile acid transport inhibitors and are 1,4-benzothiazepine and 1,5-benzothiazepine compounds corresponding to Formula I: wherein j, m, Y, Z, R1A, R1B, R2A, R2B and R6 are as defined in the specification.