4637-59-6

Upstream product

• 611-35-8 4-chloroquinoline 
• 2508-86-3 4-aminoquinoline 1-oxide 
• 56-57-5 4-nitroquinoline-N-oxide 
• 91-22-5 quinoline 
• 1613-37-2 Quinoline N-oxide 

Downstream Products

• 14547-98-9 4-methoxyquinoline-N-oxide 
• 69619-12-1 4-phenoxyquinoline N-oxide 
• 115913-62-7 4-(phenylthio)quinoline 1-oxide 
• 157563-21-8 4-(4-nitro-phenylsulfanyl)-quinoline-1-oxide 
• 4552-43-6 4-chloroquinoline-2-carbonitrile 
• 611-35-8 4-chloroquinoline 
• 74421-81-1 4-benzylquinoline 1-oxide 
• 76278-25-6 4-(4-Chloro-quinolin-2-yl)-2-phenyl-4H-oxazol-5-one 
• 75003-52-0 5-(4-Chloro-quinolin-2-yl)-3-phenyl-2-thioxo-thiazolidin-4-one 
• 110036-04-9 4-(cyanophenylthio)methylquinoline 1-oxide 
• 110036-00-5 4-chloro-2-phenylsulfonylmethylquinoline 1-oxide 
• 139366-52-2 2-phenyl-3-mesyl-furo<3,2-c>quinoline 
• 139366-51-1 2-(4-Chloro-quinolin-3-yl)-2-methanesulfonyl-1-phenyl-ethanone 
• 110036-02-7 4-Chloro-2-(toluene-4-sulfonylmethyl)-quinoline 1-oxide 

Relevant academic research and scientific papers

Reactions of 4-nitroquinoline 1-oxide with aluminum chloride

4-Nitroquinoline 1-oxide reacts with aluminum chloride to give 4-chloroquinoline 1-oxide. Aluminum chloride with 4-nitroquinoline 1-oxide forms a molecular complex in which it acts as electron acceptor and effective nucleophilic reagent (a source of chloride ions).

Electrochemical-Oxidation-Promoted Direct N-ortho-Selective Difluoromethylation of Heterocyclic N-Oxides

An efficient and green electrochemical N-ortho-selective difluoromethylation method of various quinoline and isoquinoline N-oxides has been developed. In this method, sodium difluoromethanesulfinate (HCF2SO2Na) was used as the source of the difluoromethyl moiety, and various N-ortho-selective difluoromethylation quinoline and isoquinoline N-oxides were obtained in good to excellent yields under a constant current. In addition, the reaction was easy to scale up and maintained a good yield. Preliminary mechanism studies suggested that the reaction undergoes a free-radical addition and hydrogen elimination pathway.

SMALL-MOLECULE NADPH OXIDASE 2 INHIBITORS

The invention provides compounds of Formula (II) which comprise two terminal 2-aminoquinoline moieties. They are novel and potent inhibitors of the p47phox-p22phox protein-protein interaction that can inhibit the assembly and thus activation of the multisubunit and superoxide-generating NADPH oxidase 2 complex. The compounds are therapeutically relevant as they can reduce cell damage in diseases where NADPH oxidase 2 is a major contributor to generation of reactive oxygen species (ROS) and oxidative stress.

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.

Metal-free C8-H functionalization of quinolineN-oxides with ynamides

The metal-free C8-H functionalization of quinolineN-oxides with ynamides is unveiled for the first time by the intramolecular Friedel-Crafts-type reaction of quinolyl enolonium intermediates generated from Br?nsted acid-catalyzed addition of quinolineN-ox

Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3 + 2] Cycloaddition

A transition-metal-free deoxygenative C-H amination reaction of azine-N-oxides with acyl azides is described. The initial formation of an isocyanate from the starting acyl azide via a Curtius rearrangement can trigger a [3 + 2] dipolar cycloaddition of polar N-oxide fragments to generate the aminated azine derivative. The applicability of this method is highlighted by the late-stage and sequential amination reactions of complex bioactive compounds, including quinidine and fasudil. Moreover, the direct transformation of aminated azines into various bioactive N-heterocycles illustrates the significance of this newly developed protocol.

SUBSTITUTED 2,4 DIAMINO-QUINOLINE AS NEW MEDICAMENT FOR FIBROSIS, AUTOPHAGY AND CATHEPSINS B (CTSB), L (CTSL) AND D (CTSD) RELATED DISEASES

The present invention relates to novel 2-primary amino-4-secondary amino-quinoline derivatives, their manufacture, pharmaceutical compositions comprising them and their use as medicaments. The active compounds of the present invention can be useful as a medicament in the treatment and/or the decreasing and/or the prevention of fibrosis and/or fibrosis related diseases, or for use as a medicament in the treatment and/or the decreasing and/or the prevention of the autophagy and/or autophagy related diseases and for the inhibition of the autophagy flux, or for use in the inhibition of cathepsins B (CTSB), L (CTSL) and/or D (CTSD) and/or cathepsins B (CTSB), L (CTSL) and/or D (CTSD) related diseases; with the proviso that said compounds are not to be used for the treatment of any forms of cancers.

Enantioselective Palladium(II)-Catalyzed Oxidative Aminofluorination of Unactivated Alkenes with Et4NF?3 HF as a Fluoride Source

The first asymmetric PdII-catalyzed aminofluorination of unactivated alkenes using chiral quinoline-oxazolines (Quox) as ligands has been developed. This reaction provides easy access to a wide array of enantiomerically enriched β-fluoropiperidines in good yields and with excellent enantioselectivity. Notably, Et4NF?3 HF as a readily accessible nucleophilic fluoride source was found to play an essential role in the enantioselective control, and CsOCF3 also acts a key additive to improve the excellent ee value of products.

Developing Inhibitors of the p47phox-p22phox Protein-Protein Interaction by Fragment-Based Drug Discovery

Nicotinamide adenine dinucleotide phosphate oxidase isoform 2 is an enzyme complex, which generates reactive oxygen species and contributes to oxidative stress. The p47phox-p22phox interaction is critical for the activation of the catalytical NOX2 domain, and p47phox is a potential target for therapeutic intervention. By screening 2500 fragments using fluorescence polarization and a thermal shift assay and validation by surface plasmon resonance, we found eight hits toward the tandem SH3 domain of p47phox (p47phoxSH3A-B) with KD values of 400-600 μM. Structural studies revealed that fragments 1 and 2 bound two separate binding sites in the elongated conformation of p47phoxSH3A-B and these competed with p22phox for binding to p47phoxSH3A-B. Chemical optimization led to a dimeric compound with the ability to potently inhibit the p47phoxSH3A-B-p22phox interaction (Ki of 20 μM). Thereby, we reveal a new way of targeting p47phox and present the first report of drug-like molecules with the ability to bind p47phox and inhibit its interaction with p22phox.

Visible-Light-Promoted C2 Trifluoromethylation of Quinoline N -Oxides

A photoredox catalytic strategy has been described for the direct C2 trifluoromethylation of quinoline N -oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2 tri