6274-29-9

Usage

Uses

Used in Pharmaceutical Industry:
2-amino-5-methoxy-benzenethiol is used as a chemical reagent for the synthesis of antibacterial benzothiazepines. These benzothiazepines are known for their broad-spectrum antimicrobial activity, making them valuable in the development of new antibiotics to combat drug-resistant bacterial infections.
Used in Chemical Synthesis:
In the field of organic chemistry, 2-amino-5-methoxy-benzenethiol serves as an important building block for the synthesis of various organic compounds. Its unique functional groups allow for a range of reactions, such as nucleophilic substitution, electrophilic aromatic substitution, and redox reactions, which can be harnessed to create a diverse array of molecules with potential applications in various industries.
Used in Material Science:
The unique structure of 2-amino-5-methoxy-benzenethiol also makes it a candidate for the development of new materials with specific properties. For instance, its thiol group can participate in the formation of self-assembled monolayers or multilayers on various surfaces, which could be useful in the fabrication of sensors, catalysts, or other functional materials.

InChI:InChI=1/C7H9NOS/c1-9-5-2-3-6(8)7(10)4-5/h2-4,10H,8H2,1H3

Upstream product

• 35576-56-8 6-methoxy-1,2,3-benzodithiazolium chloride 
• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 54346-87-1 2-amino-5-methoxybenzothiazole 
• 7732-36-7 bis(2-amino-5-methoxyphenyl)disulfide 
• 2293-07-4 1-(4-methoxyphenyl)thiourea 
• 104-94-9 4-methoxy-aniline 
• 1367199-65-2 BrH*C₈H₈N₂OS 
• 20265-97-8 p-anisidine hydrochloride 

Downstream Products

• 2941-72-2 6-methoxy-2-methylbenzothiazole 
• 37764-05-9 2-amino-N-(2-mercapto-4-methoxy-phenyl)-5-methyl-benzamide 
• 60598-40-5 6-anilino-9-methoxy-benzo[a]phenothiazin-5-one 
• 83516-41-0 4-Methoxy-2-(3-nitro-pyridin-2-ylsulfanyl)-phenylamine 
• 100601-17-0 threo-2-hydroxy-3-<(2-amino-5-methoxyphenyl)thio>-3-(4-methoxyphenyl)propionic acid methyl ester 
• 76273-50-2 (7-Methoxy-3-phenyl-4H-benzo[1,4]thiazin-2-yl)-phenyl-methanone 
• 22726-30-3 7-methoxy-2H-benzo[b][1,4]thiazin-3(4H)-one 
• 86328-45-2 1-(6-methoxybenzo[d]thiazol-2-yl)guanidine 
• 139356-68-6 8-Methoxy-4-(4-methoxy-phenyl)-2-phenyl-2,5-dihydro-benzo[b][1,4]thiazepine 
• 2942-13-4 6-methoxy-1,3-benzothiazole 
• 101078-75-5 2-<4-(bromomethyl)phenyl>-6-methoxybenzothiazole 
• 98120-09-3 2-(p-chlorobenzoyl)-7-methoxy-3-methyl-4H-1,4-benzothiazine 
• 124414-26-2 8-Methoxy-4-p-tolyl-2,3-dihydro-benzo[b][1,4]thiazepine-2-carboxylic acid 
• 123533-58-4 8-Methoxy-4-(4-methoxy-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepine-2-carboxylic acid 

Relevant academic research and scientific papers

A polymerizable Aggregation Induced Emission (AIE)-active dye with remarkable pH fluorescence switching based on benzothiazole and its application in biological imaging

In recent years, Aggregation Induced Emission (AIE)-active fluorescent materials have been attracting considerable attention because they play an important role in clinical medicine, photoelectricity, environmental science, biological imaging, and sensors. In this contribution, a novel tetraphenylethylene (TPE) derivative of 2-(4-(1,2,2-triphenylvinyl)benzene) benzothiazole methacrylate (TPBMA) monomer was synthesized by a Suzuki coupling and an acylation reaction using TPE and benzothiazole as structural units, whose maximum emission wavelength respectively appeared at 506 nm in neutral medium and 579 nm in acidic medium with excellent pH sensitivity, and it could change repeatedly at 500 nm and 579 nm under HCl/NH3 fuming, indicating the reversible fluorescence conversion property. As compared with the TPB dye, the emission wavelength of TPBMA spectra has an obvious red-shift, which is consistent with the transition energy level difference (△E) of highest occupied molecular orbital (HOMO) and lowest unoccupied orbital (LUMO) situation by quantum chemistry calculation. Subsequently, the copolymers PEG-TB were successfully prepared by RAFT polymerization of TPBMA and poly (ethylene glycol) monomethacrylate (PEGMA), and their molecular weight (Mw) was about 2.12 × 104 with a narrow polydispersity index (PDI). From the 1H NMR analysis, the actual fraction of TPBMA in the PEG-TB copolymers increased to 22.6% from 17.4% when the feed ratio of TBMTA changed to 25.0% from 20.0%. The obtained PEG-TB could self-assemble into fluorescent organic nanoparticles (FONs) with 100–150 nm diameter in aqueous solution, and their fluorescence intensity increased gradually with the increase of water fraction in the THF solution, indicating the obvious AIE behavior. Moreover, the as-prepared PEG-TB FONs exhibited the prospective potential in the field of biological imaging due to their low cytotoxicity, excellent biocompatibility and easy cells absorption.

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.

A Novel Difluoroacetic Acid Derivatives Compound, and Composition Comprising the Same

The present invention relates to a novel difluoroacetic acid derivative compound and a composition for various uses containing the same, wherein the difluoroacetic acid derivative compound can not only act as an agonist activating one among PPARandalpha;, andbeta; or andgamma;, but also can exhibit double efficacy or triple efficacy. Therefore, the difluoroacetic acid derivative compound can more effectively prevent, alleviate or treat metabolic diseases in which PPARs involves, and further exhibits whitening and wrinkle alleviation activity, and anti-inflammatory and antioxidant effects, thereby being able to be usefully utilized as various compositions.COPYRIGHT KIPO 2020

Metal-chelating benzothiazole multifunctional compounds for the modulation and 64Cu PET imaging of Aβ aggregation

While Alzheimer's Disease (AD) is the most common neurodegenerative disease, there is still a dearth of efficient therapeutic and diagnostic agents for this disorder. Reported herein are a series of new multifunctional compounds (MFCs) with appreciable affinity for amyloid aggregates that can be potentially used for both the modulation of Aβ aggregation and its toxicity, as well as positron emission tomography (PET) imaging of Aβ aggregates. Firstly, among the six compounds tested HYR-16 is shown to be capable to reroute the toxic Cu-mediated Aβ oligomerization into the formation of less toxic amyloid fibrils. In addition, HYR-16 can also alleviate the formation of reactive oxygen species (ROS) caused by Cu2+ ions through Fenton-like reactions. Secondly, these MFCs can be easily converted to PET imaging agents by pre-chelation with the 64Cu radioisotope, and the Cu complexes of HYR-4 and HYR-17 exhibit good fluorescent staining and radiolabeling of amyloid plaques both in vitro and ex vivo. Importantly, the 64Cu-labeled HYR-17 is shown to have a significant brain uptake of up to 0.99 ± 0.04 percentID per g. Overall, by evaluating the various properties of these MFCs valuable structure-activity relationships were obtained that should aid the design of improved therapeutic and diagnostic agents for AD. This journal is

P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate

The direct reductive N-arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N-methylanilines from various stable isotopologues of nitromethane (i.e., CD3NO2, CH315NO2, and 13CH3NO2), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.

Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones

A straightforward method to prepare 1,5-benzothiazepines was reported. Catalyzed by a Rh/Zhaophos complex, unsaturated cyclic NH lactams with a medium-size ring were hydrogenated smoothly, giving remarkably high enantioselectivities. The sulfur atom in the substrates did not bring an inhibition which was observed with commercially available bisphosphine ligands. This method was successfully applied in the scale-up synthesis of (R)-(-)-thiazesim.

PROTEOLYSIS TARGETING CHIMERIC (PROTAC) COMPOUND WITH E3 UBIQUITIN LIGASE BINDING ACTIVITY AND TARGETING ALPHA-SYNUCLEIN PROTEIN FOR TREATING NEURODEGENERATIVE DISEASES

The present disclosure relates to bifunctional compounds, which find utility as modulators of alpha-synuclein (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand which binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/ inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure. Such diseases or disorders are alpha-synucleinopathies or neurodegenerative diseases associated with alpha-synuclein accumulation and aggregation, such as e.g. Parkinson Disease, Alzheimer's Disease, dementia, dementia with Lewy bodies or multiple system atrophy, in particular Parkinson's Disease.

Synthesis and crystal structure of 7-bromo-3,3-dibutyl-8-methoxy-5-phenyl-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one

7-Bromo-3,3-dibutyl-8-methoxy-5-phenyl-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one is prepared from 6-methoxybenzo[d]thiazol-2-amine and 2-(bromomethyl)-2-butylhexanoic acid as the key starting materials via five simple steps including hydrolysis, substit

Convenient and efficient synthesis of novel 11: H -benzo[5,6][1,4]thiazino[3,4- a] isoindol-11-ones derived from 2-bromo-(2/3-substitutedphenyl)-1 H -indene-1,3(2 H)-diones

An unprecedented formation of 11H-benzo[5,6][1,4]thiazino[3,4-a]isoindol-11-ones through a one-step reaction of differently substituted 2-aminobenzenethiols and 2-bromo-(2/3-substitutedphenyl)-1H-indene-1,3(2H)-diones in freshly dried ethanol under reflux conditions has been investigated. This unique transformation probably occurs through an initial nucleophilic substitution followed by ring opening and subsequent intramolecular cyclization. The structures of all the synthesized benzo[1,4]thiazino isoindolinones were established by FTIR, 1H NMR, 13C NMR, HRMS, and X-ray crystallographic analysis. This approach was found to be simple and convenient and provides several advantages such as substantial atom economy, short reaction time and operational simplicity.

Compounds with high selectivity to tau aggregates, tau-targeting probe comprising the same, and preparation method thereof

The present invention relates to: a compound represented by chemical formula 1, which exhibits excellent binding force to tau aggregates, thereby being useful for early diagnosis of degenerative brain diseases including dementia, and for preventing and treating the same; a method for manufacturing the same; and a pharmaceutical composition comprising the same. The compound according to the present invention exhibits a high selectivity to tau aggregates compared to beta amyloid, and thus the compound can be usefully used for the early diagnosis and prevention or treatment of diseases related to tau aggregates including dementia.COPYRIGHT KIPO 2019