4053-34-3

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 7600, 1978 DOI: 10.1021/ja00492a028

Upstream product

• 91-62-3 6-methylquinoline 
• 4053-42-3 6-methylquinoline-N-oxide 
• 102-92-1 cinnamoyl chloride 
• 106-49-0 p-toluidine 
• 134430-88-9 (2E)-N-(4-methylphenyl)-3-phenylprop-2-enamide 
• 140-88-5 ethyl acrylate 
• 1810-66-8 6-bromo-2-quinolone 
• 1810-71-5 6-bromo-2-chloroquinoline 
• 4295-11-8 2-chloro-6-methylquinoline 
• 29289-13-2 2-iodo-4-methylaniline 
• 53165-17-6 N-(2-formyl-4-methylphenyl)acetamide 
• 142219-58-7 N-(2-bromo-4-methylphenyl)cinnamamide 
• 6876-68-2 N-(4-methylphenyl)-3-phenyl-2-propenamide 
• 60-35-5 acetamide 

Downstream Products

• 608-05-9 5-methyl-indole-2,3-dione 
• 20150-83-8 6-methyl-1,2,3,4-tetrahydroquinolin-2-one 
• 4295-11-8 2-chloro-6-methylquinoline 
• 123637-16-1 (S)-2-{4-[(2-Chloro-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid 
• 141376-53-6 4-[5-fluoro-3-(1,2-hydro-2-oxoquinolin-6-ylmethoxy)phenyl]-4-methoxytetrahydropyran 
• 133739-66-9 6-<<3-fluoro-5-(4-methoxy-3,4,5,6-tetrahydro-2H-pyran-4-yl)phenoxy>methyl>-1-<(pivaloyloxy)methyl>quinol-2-one 
• 1562370-42-6 C₂₀H₂₀FN₃O 
• 1562370-50-6 C₂₀H₂₀FN₃O 
• 1562370-49-3 C₂₁H₂₂FN₃O 
• 1562370-51-7 C₂₂H₂₄FN₃O 

Relevant academic research and scientific papers

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

Visible light-induced one-pot synthesis of CF3/CF2-substituted cyclobutene derivatives

An efficient one-pot approach for the controllable synthesis of trifluoromethyl/gem-difluoromethylene substituted cyclobutene derivatives has been developed. The mechanism may involve visible light-induced [2+2]-cycloaddition of quinolinones with 1-bromo-1-trifluoromethylethene, followed by base-promoted dehydrobromination, [1,3]-H shift and further dehydrofluorination. A variety of CF3/CF2-substituted cyclobutenes that are currently difficult to obtain are afforded in good yields in this protocol, which may find its way into future fluorinated cyclobutene preparation.

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

REDUCTION OF PRO-INFLAMMATORY HDL USING A LEUKOTRIENE INHIBITOR

A method involving the administration of a therapeutically effective amount of a leukotriene inhibitor, a pharmaceutically acceptable salt, a pharmaceutically acceptable N-oxide, a pharmaceutically active metabolite, a pharmaceutically acceptable prodrug, or pharmaceutically acceptable solvate thereof to a human for reducing a level of pro-inflammatory HDL in the human. Various examples of leukotriene inhibitors, including 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin- 3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2, 2-dimethyl-propionic acid, are disclosed for administration for the reduction of pro-inflammatory HDL in a human. Reduction of pro-inflammatory HDL by the leukotriene inhibitor may include conversion of at least a portion of pro-inflammatory HDL to anti-inflammatory HDL.

Palladium-catalyzed synthesis of quinolin-2(1: H)-ones: the unexpected reactivity of azodicarboxylate

Quinolin-2(1H)-one is a useful structure unit present in a wide range of natural products and pharmaceuticals. A Pd(ii)-catalyzed synthesis of quinolin-2(1H)-ones from quinoline N-oxides was developed with azodicarboxylates which act as both the activating agent and oxidant. The reaction proceeded under mild conditions and no protection against air and moisture was needed.

A nitrogen oxide C2 - bit hydroxylated method (by machine translation)

The present invention relates to nitrogen oxide C2 - bit hydroxylated method, in particular under reflux conditions in dichloroethane, three pyrrole alkyl bromide (PyBrop) [...] phosphate, sodium acetate, water and nitrogen oxides produced by the reaction of hydroxyl-substituted product. The process has simple operation, mild condition, high reaction selectivity, substrate wide applicability, high yield and the like. The application for the first time using this method to synthesize a series of 2 - hydroxyquinoline, 2 - hydroxy pyridine and 1 - hydroxy isoquinoline compound, in the establishment of the compounds of the library synthesis application have broad prospects. (by machine translation)

Quinoline derivatives and their use

The invention discloses a quinoline derivative and a usage thereof, a compound with a structure as shown in a formula (I) and or a pharmaceutically acceptable salt of the compound. The compound or the pharmaceutically acceptable salt thereof disclosed by the invention can be applied to the field of preparation of drugs for preventing or treating tumors.

Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1H)-Quinolones Induced by Visible Light Irradiation

In the presence of a chiral thioxanthone catalyst (10 mol %) the title compounds underwent a clean intermolecular [2 + 2] photocycloaddition with electron-deficient olefins at λ = 419 nm. The reactions not only proceeded with excellent regio- and diastereoselectivity but also delivered the respective cyclobutane products with significant enantiomeric excess (up to 95% ee). Key to the success of the reactions is a two-point hydrogen bonding between quinolone and catalyst enabling efficient energy transfer and high enantioface differentiation. Preliminary work indicated that solar irradiation can be used for this process and that the substrate scope can be further expanded to isoquinolones.

Iron-catalyzed aerobic oxidative cleavage of the C-C σ-bond using air as the oxidant: Chemoselective synthesis of carbon chain-shortened aldehydes, ketones and 1,2-dicarbonyl compounds

A simple iron-catalyzed aerobic oxidative C-C σ-bond cleavage of ketones has been developed. Readily available and environmentally benign air is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, chemoselectively yielding carbon chain-shortened aldehydes, ketones and 1,2-dicarbonyl compounds without overoxidation.

2-aminoquinoline-based compounds for potent and selective neuronal nitric oxide synthase inhibition

Various 2-aminoquinoline compounds as can be used, in vivo or in vitro, for selective inhibition of neuronal nitric oxide synthase.