33264-82-3

Usage

Uses

Used in Coordination Chemistry:
2-Amino-5-fluorobenzenethiol is used as a chelating ligand in coordination chemistry, where its ability to form stable complexes with metal ions is leveraged for various applications, such as catalysis and the development of new materials.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-Amino-5-fluorobenzenethiol is used as an intermediate in the synthesis of various drugs. Its presence in the molecular structure can influence the pharmacological properties of the final product, potentially enhancing efficacy or selectivity.
Used in Organic Compounds Synthesis:
2-Amino-5-fluorobenzenethiol is utilized as an intermediate in the synthesis of a wide range of organic compounds, contributing to the development of new chemical entities with diverse applications.
Used in Dye and Pigment Production:
In the dye and pigment industry, 2-Amino-5-fluorobenzenethiol is used in the production of various colorants, where its aromatic structure and functional groups contribute to the color properties and stability of the dyes and pigments.
Used in Rubber Chemicals Production:
2-Amino-5-fluorobenzenethiol is employed in the production of rubber chemicals, where it may be used to modify the properties of rubber, such as improving its resistance to heat, oxidation, or other environmental factors.
Used in Medicine:
In the medical field, 2-Amino-5-fluorobenzenethiol has potential applications due to its unique chemical properties, which may be harnessed for the development of new therapeutic agents or diagnostic tools.
Used in Biochemistry:
In biochemistry, 2-Amino-5-fluorobenzenethiol may be used in the study of biological processes or the development of biochemical assays, taking advantage of its reactivity and functional groups.
Used in Material Science:
In material science, 2-Amino-5-fluorobenzenethiol can be used in the development of new materials with specific properties, such as improved conductivity, stability, or responsiveness to environmental stimuli.

InChI:InChI=1/C6H6FNS/c7-4-1-2-5(8)6(9)3-4/h1-3,9H,8H2

Upstream product

• 348-40-3 2-amino-6-fluoro-1,3-benzothiazole 
• 118220-71-6 6-fluorobenzothiazole 
• 63755-07-7 bis(2-amino-5-fluorophenyl)disulfide 
• 371-40-4 4-fluoroaniline 
• 2146-07-8 p-fluoroaniline hydrochloride 
• 459-05-2 (4-fluoro-phenyl)-thiourea 
• 399-73-5 6-fluoro-2-methylbenzo[d]thiazole 
• 399-36-0 N-(2,4-difluoro-phenyl)-acetamide 
• 367-25-9 2,4-difluorophenylamine 

Downstream Products

• 118220-71-6 6-fluorobenzothiazole 
• 60598-38-1 6-anilino-9-fluoro-benzo[a]phenothiazin-5-one 
• 124414-23-9 2-Carboxy-2,3-dihydro-4-(p-tolyl)-8-fluoro-1,5-benzothiazepine 
• 123533-60-8 4-(p-Anisyl)-2-carboxy-2,3-dihydro-8-fluoro-1,5-benzothiazepine 
• 116625-97-9 4-(p-chlorophenyl)-8-fluoro-2-(p-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepine 
• 135517-94-1 (3,4-Dimethoxy-phenyl)-(7-fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 100492-87-3 (2S,3S)-8-Fluoro-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 100492-85-1 (2S,3S)-8-Fluoro-3-hydroxy-2-p-tolyl-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 137482-42-9 (2-Bromo-phenyl)-(7-fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 135517-92-9 (2,4-Dimethoxy-phenyl)-(7-fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 121364-18-9 Biphenyl-4-yl-(7-fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 124050-14-2 2-chloromethyl-6-fluorobenzothiazole 

Relevant academic research and scientific papers

Synthesis, structural characterization, docking, lipophilicity and cytotoxicity of 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-alkyl carbamates, novel acetylcholinesterase and butyrylcholinesterase pseudo-irreversible inhibitors

In the current study, sixteen novel derivatives of (R)-1-(6-fluorobenzo[d]thiazol-2-yl)ethanamine were synthesized as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. Chemical structures together with purity of the synthesized compounds were substantiated by IR, 1H, 13C, 19F NMR, high resolution mass spectrometry and elemental analysis. The optical activities were confirmed by optical rotation measurements. The synthesized compounds were evaluated for their AChE and BChE inhibitory activities. In addition, the cytotoxicity of the most active compounds was investigated against human cell lines employing XTT tetrazolium salt reduction assay and xCELLigence system allowing a label-free assessment of the cells proliferation. Our results demonstrated that the inhibitory mechanism was confirmed to be pseudo-irreversible, in line with previous studies on carbamates. Compounds indicated as 3b, 3d, 3l and 3n showed the best AChE inhibitory activity of all the evaluated compounds and were up to tenfold more potent than standard drug rivastigmine. The binding mode was determined using state-of-the-art covalent docking and scoring methodology. The obtained data clearly demonstrated that 3b, 3d, 3l and 3n benzothiazole carbamates possess high inhibitory activity against AChE and BChE and concurrently negligible cytotoxicity. In conclusion, our results indicate, that these derivatives could be promising in an effective therapeutic intervention for Alzheimer's disease.

Synthesis and evaluation of novel 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibition agents

Anaplastic lymphoma kinase (ALK) targeted therapies have demonstrated remarkable efficacy in ALK-positive lung adenocarcinomas. Here we synthesized and evaluated sixteen new 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibitors. The optimal compound 9e exhibited excellent antiproliferative activity against non-small cell lung cancer NCI-H2228 cells, which is better than that of Brigatinib and similar to Ceritinib. Mechanism study revealed that the optimal compound 9e decreased the mitochondrial membrane potential and arrested NCI-H2228 cells in the G0/G1 phase, finally resulting in cellular apoptosis. It is interesting that 9e could effectively inhibit the migration of NCI-H2228 cells and may be a promising leading compound for chemotherapy of metastatic cancer.

AcOH-mediated aerobic oxidative synthesis of 2-thioalkylbenzothiazoles via a three-component reaction

An AcOH-mediated three-component reaction of 2-aminothiophenols, α,β-unsaturated aldehydes, and thiophenols to prepare the high value-added 2-thioalkylbenzothiazoles was developed. The reaction was conducted under metal-free conditions, where oxygen served as the terminal oxidant. In addition, this strategy is tolerant of kinds of functional groups, providing efficient access to a variety of functionalized benzothiazole derivatives in moderate to good yields. What's more, this reaction has complete regioslectivity and provides a powerful method for building complex molecules.

COMPOUNDS FOR THE MODULATION OF MYC ACTIVITY

The present invention provides novel compounds of Formula (I) and Formula (II) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are methods and kits involving the compounds or compositions for treating or preventing proliferative diseases, e.g., cancers (e.g., breast cancer, prostate cancer, lymphoma, lung cancer, pancreatic cancer, ovarian cancer, neuroblastoma, or colorectal cancer), benign neoplasms, angio genesis, inflammatory diseases, fibrosis (e.g., polycystic kidney disease), autoinflammatory diseases, and autoimmune diseases in a subject.

Synthesis, structural characterization, antimicrobial and antifungal activity of substituted 6-fluorobenzo[d]thiazole amides

A series of novel 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-substituted phenyl amides was synthesized by the condensation reaction of (1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethanamine with substituted benzoyl chlorides under mild conditions. Their structures were confirmed by 1H NMR, 13C NMR and 19F NMR spectra, elemental analyses and in three cases also by single-crystal X-ray diffraction techniques. The optical activities were confirmed by optical rotation measurements. All the synthesized compounds were screened for antibacterial and antifungal activity against a variety of bacterial and fungal strains. Some of the compounds reveal antibacterial and antifungal activity comparable or slightly better to that of chloramphenicol, cefoperazone and amphotericin B used as medicinal standards.

Synthesis, characterization and in vitro antimicrobial assessment of some novel 4H-1, 4-benzothiazines and their sulfone derivatives

In recent years, synthesis and biological evaluation of novel 4H-1,4-benzothiazines and their sulfone derivatives have gained momentum due to their medicinal and industrial importance. Our studies focused on the design and synthesis of new antimicrobial agents, and for this purpose a series of novel 4H-1,4-benzothiazines and their sulfone derivatives were synthesized and their in vitro antimicrobial assessment was carried out against a representative panel of Gram-positive and Gram-negative bacteria strains and selected fungi species. The reported 4H-1,4-benzothiazines were prepared by condensation followed by oxidative cyclization of substituted 2-aminobenzenethiols with compounds containing active methylene groups. It is believed that the reaction proceeds via intermediary of the enaminoketone system. The sulfone derivatives were synthesized by oxidation of 4H-1,4-benzothiazines using 30% hydrogen peroxide in glacial acetic acid. Structure determination was done by spectral and elemental investigations.

Fluorescence properties of 5-(5,6-dimethoxybenzothiazol-2-yl)-2′- deoxyuridine (dbtU) and oligodeoxyribonucleotides containing d btU

We describe the synthesis and photophysical properties of 11 substituted 5-(benzothiazol-2-yl)-2′-deoxyuridine derivatives and oligodeoxyribonucleotides (ODNs) containing 5-(5,6-dimethoxybenzothiazol-2-yl)- 2′-deoxyuridine (dbtU), which was the strongest fluorescent derivative among those prepared. The fluorescence properties of dbtU itself and ODNs containing dbtU show the same tendency of being weaker in both neutral and acidic solution and stronger in basic solution. The ODNs (15mer) containing 16 combinations of 5′-XbtU-3′ and 5′-btUY-3′, where X, Y = A, T, G, or C, were synthesized, and their fluorescence intensity and quantum yield in basic solution were compared. On average, only the ODN with the 5′-G btU-3′ sequence shows a 7.9-fold lower fluorescence intensity than the other sequences. Ab initio calculations of 5′-G btU-3′ and 5′-btUG-3′ as models under basic conditions suggest that the lower fluorescence of the ODN containing the 5′-GbtU-3′ sequence is caused by a wider overlap between stacked guanine (Gua) and btUra than that of the 5′- btUG-3′ sequence and that the HOMO is delocalized not only on btUra but also on Gua.

NOVEL COMPOUNDS

The invention relates to tricyclic derivatives, and their use in treating diseases and conditions mediated by antagonism of the mGluR5 receptor, in particular substance related disorders. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

Syntheses and evaluation of fluorinated benzothiazole anilines as potential tracers for β-amyloid plaques in Alzheimer's disease

[11C]2-(4′-(Methylamino)phenyl)-6-hydroxybenzothiazole ([11C]PIB) is a most potential PET tracer for detecting the β-amyloid plaques in Alzheimer's disease. Here the syntheses of three fluorinated PIB, namely 2-(4′-(methylamino)phenyl)-6-fluoroethoxybenzothiazole (O-FEt-PIB), 2-(4′-(methylamino)phenyl)-6-fluoro-benzothiazole (F-N-Me) and 2-(4′-(dimethylamino)phenyl)-6-fluorobenzo-thiazole (F-N,N-Me), and the radiosynthesis of one corresponding 18F-labeled PIB compound, [18F]O-FEt-PIB, as well as their in vitro/in vivo biological characters were reported. The structures of the products were confirmed by IR, 1H NMR, EI/ESI-MS, elemental analysis and HRMS techniques. The radiolabeled product was characterized by radio-TLC and radio-HPLC and purified by semi-preparative radio-HPLC. The suitable biological characters showed these tracers were potential to be developed as probes for detecting β-amyloid plaques in Alzheimer's disease.

Synthesis of 7-chloro-5-trifluoromethyl/7-fluoro/7-trifluoromethyl-4H-1,4-benzothiazines as antimicrobial agents

7-Chloro-5-trifluoromethyl/7-fluoro/7-trifluoromethyl-4H-1,4-benzothiazines have been synthesized by 2-amino-5-fluoro/5-trifluoromethyl/5-chloro-3-trifluoromethyl benzenethiols condensed with β-diketone/β-ketoesters in the presence of DMSO involving oxidative cyclization. Pharmacological activities have also been included.