4295-11-8

Usage

InChI:InChI=1/C10H8ClN/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3

Upstream product

• 107734-14-5 4-methyl-2-vinylaniline 
• 503-38-8 trichloromethyl chloroformate 
• 109-69-3 n-Butyl chloride 
• 583-68-6 2-bromo-p-toluidine 
• 6876-68-2 N-(4-methylphenyl)-3-phenyl-2-propenamide 
• 1810-71-5 6-bromo-2-chloroquinoline 
• 74-88-4 methyl iodide 
• 1810-66-8 6-bromo-2-quinolone 
• 106-49-0 p-toluidine 
• 29969-49-1 1,6-dimethyl-2(1H)-quinolinone 
• 91-62-3 6-methylquinoline 
• 4053-42-3 6-methylquinoline-N-oxide 
• 123637-77-4 6-bromomethyl-2-chloro-quinoline 
• 68882-99-5 2-ethenyl-4-methylacetanilide 

Downstream Products

• 4053-34-3 6-methylquinolin-2(1H)-one 
• 1001608-59-8 5-[2-(2-fluoro-phenyl)-quinolin-6-yl]-4H-thieno[3,2-b]pyrrole-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

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.

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.

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

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.

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.

Development of a facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines

A facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines via N-methylbenzopyridin-α-ones was developed. α-Unsubstituted benzopyridines were converted easily into the corresponding N-methylbenzopyridin-α-ones, which were halogenated using PPh3-TCICA or PPh3-DBICA without using solvent to give α-halobenzopyridines.

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

Since high levels of nitric oxide (NO) are implicated in neurodegenerative disorders, inhibition of the neuronal isoform of nitric oxide synthase (nNOS) and reduction of NO levels are therapeutically desirable. Nonetheless, many nNOS inhibitors mimic l-arginine and are poorly bioavailable. 2-Aminoquinoline-based scaffolds were designed with the hope that they could (a) mimic aminopyridines as potent, isoform-selective arginine isosteres and (b) possess chemical properties more conducive to oral bioavailability and CNS penetration. A series of these compounds was synthesized and assayed against purified nNOS enzymes, endothelial NOS (eNOS), and inducible NOS (iNOS). Several compounds built on a 7-substituted 2-aminoquinoline core are potent and isoform-selective; X-ray crystallography indicates that aminoquinolines exert inhibitory effects by mimicking substrate interactions with the conserved active site glutamate residue. The most potent and selective compounds, 7 and 15, were tested in a Caco-2 assay and showed good permeability and low efflux, suggesting high potential for oral bioavailability.

A practical and mild chlorination of fused heterocyclic N-oxides

Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated.

2-[3H-THIAZOL-2-YLIDINEMETHYL]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE

The present invention pertains to certain 2-[3H-thiazol-2-ylidinemethyl]pyridine compounds and analogs thereof, which, inter alia, inhibit cell proliferation, treat cancer, etc., and more specifically to compounds of the following formula, wherein RA1, RA2, RA3, RA4, RB1, RB2, RNA, RNB, and X? are as defined herein: The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit cell proliferation, and in the treatment of proliferative conditions such as cancer, etc.

Bicyclic aromatic substituted pyridone derivative

Disclosed is a compound represented by the formula (I): Wherein R1 and R2 independently represent a hydrogen atom, a lower alkyl group or the like; X1, X2 and X3 independently represent a methine group or a nitrogen atom; Y1 and Y3 independently represent a single bond, —O— or the like; Y2 represents a lower alkylene group or the like; W1 to W4 independently represent a single bond, a methylene group or the like; L represents a single bond, a methylene group or the like; Z1 and Z2 independently represent a single bond, a C1-4 alkylene group or the like; Ar1 represents an aromatic carbocyclic ring or the like; and Ar2 represents a bicyclic aromatic carbocyclic ring or the like. The compound is useful as a pharmaceutical for a central disease, a cardiovascular disease or a metabolic disease.