15450-72-3

Usage

Uses

Used in Pharmaceutical Research:
(2-oxo-1H-quinolin-8-yl) acetate is used as an intermediate in medicinal chemistry and drug design for the creation of biologically active compounds and potential pharmaceutical agents. Its unique structure and reactivity contribute to its importance in this field.
Used in Organic Synthesis:
(2-oxo-1H-quinolin-8-yl) acetate is used as a versatile reagent in various organic synthesis processes, allowing for the development of a range of chemical compounds.
Used in Chemical and Industrial Processes:
Due to its versatile nature and reactivity, (2-oxo-1H-quinolin-8-yl) acetate may also have applications in a variety of other chemical and industrial processes, where its unique properties can be utilized for specific purposes.

InChI:InChI=1/C11H9NO3/c1-7(13)15-9-4-2-3-8-5-6-10(14)12-11(8)9/h2-6H,1H3,(H,12,14)

Upstream product

• 15450-76-7 quinoline-2,8-diol 
• 108-24-7 acetic anhydride 
• 1127-45-3 8-Hydroxyquinoline-N-oxide 
• 148-24-3 8-quinolinol 
• 15450-76-7 8-Hydroxy-1H-quinolin-2-one 
• 2598-29-0 8-acetyloxyquinoline 
• 103368-17-8 Acetic acid 1-oxy-quinolin-8-yl ester 
• 84-88-8 8-quinolinol-5-sulfonic acid 

Downstream Products

• 139399-61-4 2-bromo-8-hydroxyquinoline 
• 201301-82-8 8-acetoxy-2-[2-(4-phenylphenyl)-2-oxoethoxy]quinoline 
• 15450-76-7 8-Hydroxy-1H-quinolin-2-one 
• 103368-28-1 2-(8-Hydroxy-2-oxo-2H-quinolin-1-yl)-propionic acid 
• 956235-09-9 5-acetyl-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one 
• 1254102-83-4 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one 
• 1254102-84-5 5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one 
• 1254098-87-7 4-[({5-[2-({[4-({[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}methyl)phenyl]methyl}carbamoyl)ethyl]-2-phenylphenyl}carbamoyl)oxy]-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 93609-84-8 5-acetyl-8-benzyloxy-1H-quinolin-2-one 
• 100331-89-3 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one 
• 530084-79-8 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one 
• 1254102-12-9 (R)-5-(2-azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one 
• 1254097-58-9 4-({[5-(2-{[4-({[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}methyl)phenyl]carbamoyl}ethyl)-2-phenylphenyl]carbamoyl}oxy)-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 1254098-73-1 4-[({5-[(8-{[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}octyl)oxy]-2-phenylphenyl}carbamoyl)oxy]-1,1-dimethylpiperidin-1-ium trifluoroacetate 

Relevant academic research and scientific papers

O-prenylated carbostyrils as a novel class of 15-lipoxygenase inhibitors: Synthesis, characterization, and inhibitory assessment

Catalyzed peroxidation of unsaturated lipid in animals and plants intimately is linked to the activity of 15-Lipoxygenase enzymes. Lipoxygenases (LOXs) are well known to play an important role in many acute and chronic syndromes such as inflammation, asthma, cancer, and allergy. In this study, a series of mono prenyloxycarbostyrils were synthesized and evaluated as potential inhibitors of soybean 15-Lipoxygenase (SLO) and their inhibitory potencies were compared to mono prenyloxycoumarins which had been reported in the previous works. The synthetic compounds inhibit lipoxygenase enzyme by competitive mechanism like the prenyloxy coumarins. The results showed that position and length of the prenyl moiety play the important role in lipoxygenase inhibitory activity. Among all of the synthetic compounds (coumarin and carbostyril derivatives), 5-farnesyloxycoumarin and 8-farnesyloxycarbostyril demonstrated the best inhibitory activity by IC50?values of 1.1?μM and 0.53?μM, respectively.

Selenophenol quinoline derivative as well as preparation method and application thereof

The invention discloses a selenophenol quinoline derivative as well as a preparation method and application thereof. The structure of the selenophenol quinoline derivative is shown as a formula I, a formula II or a formula III, wherein R1 is hydrogen, a C1-6 alkyl group, a C1-6 alkoxy group, a substituted ketone group, a phenyl group, a benzyl group, a substituted phenyl group or a substituted benzyl group; R1 is a monovalent metal cation; R2 is one or more of hydrogen, halogen, a C1-4 alkyl group, a C1-4 alkoxy group or a C1-4 haloalkyl group; R3 is a substituted five-membered heterocyclicring or a substituted six-membered heterocyclic ring; and a heteroatom is one or more of N, O, S or Se. The compound disclosed by the invention is novel in structure, simple in preparation process and relatively good in inhibition effect on various cancer cells, particularly the compounds 34, 44, 45, 98, 104, 115 and 116 have excellent inhibition effects on various cancer cells, the effects of the compounds are equivalent to those of a positive control DDP, and the compounds can be used to prepare anti-cancer drugs to be applied under 5 [mu]M or below, so that the prospect is wide.

Discovery of β-arrestin-biased β2-adrenoceptor agonists from 2-amino-2-phenylethanol derivatives

β-Arrestins are a small family of proteins important for signal transduction at G protein-coupled receptors (GPCRs). β-Arrestins are involved in the desensitization of GPCRs. Recently, biased ligands possessing different efficacies in activating the G protein- versus the β-arrestin-dependent signals downstream of a single GPCR have emerged, which can be used to selectively modulate GPCR signal transduction in such a way that desirable signals are enhanced to produce therapeutic effects while undesirable signals of the same GPCR are suppressed to avoid side effects. In the present study, we evaluated agonist bias for compounds developed along a drug discovery project of β2-adrenoceptor agonists. About 150 compounds, including derivatives of fenoterol, 2-amino-1-phenylethanol and 2-amino-2-phenylethanol, were obtained or synthesized, and initially screened for their β-adrenoceptor-mediated activities in the guinea pig tracheal smooth muscle relaxation assay or the cardiomyocyte contractility assay. Nineteen bioactive compounds were further assessed using both the HTRF cAMP assay and the PathHunter β-arrestin assay. Their concentration-response data in stimulating cAMP synthesis and β-arrestin recruitment were applied to the Black–Leff operational model for ligand bias quantitation. As a result, three compounds (L-2, L-4, and L-12) with the core structure of 5-(1-amino-2-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one were identified as a new series of β-arrestin-biased β2-adrenoceptor agonists, whereas salmeterol was found to be Gs-biased. These findings would facilitate the development of novel drugs for the treatment of both heart failure and asthma.

Novel 2, 8-bit derivatives of quinolines attenuate Pseudomonas aeruginosa virulence and biofilm formation

Signal molecules are stimulators of multiple quroum-sensing virulence and biofilm formation. Small molecule analogues have been suspected as a potent inhibitor in therapeutic strategy. Herein, we synthesized a series of small molecule compounds from the 2

CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE

The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.

Organic optoelectronic functional material and application thereof

The invention belongs to the field of organic electroluminescent devices, and discloses an organic electroluminescent material containing a diquinolyl structure and application of the organic electroluminescent material. By using the organic electroluminescent material provided by the invention as an electron transport material, the produced device has good electron mobility and relatively-balanced current carrier transmission property, and the improvement efficiency of the device is facilitated. In addition, the organic electroluminescent material provided by the invention also can be furtherblended with a hole type main body material so as to form an exciplex; by using the exciplex as a co-subject material, the efficiency and the stability of the produced device are both improved obviously.

Synthesis and evaluation of radioiodinated 1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}piperidin-4-amine derivatives for platelet-derived growth factor receptor β (PDGFRβ) imaging

Platelet-derived growth factor receptor β (PDGFRβ) is a transmembrane tyrosine kinase receptor and it is upregulated in various malignant tumors. Radiolabeled PDGFRβ inhibitors can be a convenient tool for the imaging of tumors overexpressing PDGFRβ. In this study, [125I]-1-{5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinoline-8-yl}piperidin-4-amine ([125I]IIQP) and [125I]-N-3-iodobenzoyl-1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}-piperidin-4-amine ([125I]IB-IQP) were designed and synthesized, and their potential as PDGFRβ imaging agents was evaluated. In cellular uptake experiments, [125I]IIQP and [125I]IB-IQP showed higher uptake by PDGFRβ-positive cells than by PDGFRβ-negative cells, and the uptake in PDGFRβ-positive cells was inhibited by co-culture with PDGFRβ ligands. The biodistribution of both radiotracers in normal mice exhibited hepatobiliary excretion as the main route. In mice inoculated with BxPC3-luc (PDGFRβ-positive), the tumor uptake of radioactivity at 1 h after the injection of [125I]IIQP was significantly higher than that after the injection of [125I]IB-IQP. These results indicated that [125I]IIQP can be a suitable PDGFRβ imaging agent. However, further modification of its structure will be required to obtain a more appropriate PDGFRβ-targeted imaging agent with a higher signal/noise ratio.

Site-specific tagging proteins with a rigid, small and stable transition metal chelator, 8-hydroxyquinoline, for paramagnetic NMR analysis

Design of a paramagnetic metal binding motif in a protein is a valuable way for understanding the function, dynamics and interactions of a protein by paramagnetic NMR spectroscopy. Several strategies have been proposed to site-specifically tag proteins with paramagnetic lanthanide ions. Here we report a simple approach of engineering a transition metal binding motif via site-specific labelling of a protein with 2-vinyl-8-hydroxyquinoline (2V-8HQ). The protein-2V-8HQ adduct forms a stable complex with transition metal ions, Mn(II), Co(II), Ni(II), Cu(II) and Zn(II). The paramagnetic effects generated by these transition metal ions were evaluated by NMR spectroscopy. We show that 2V-8HQ is a rigid and stable transition metal binding tag. The coordination of the metal ion can be assisted by protein sidechains. More importantly, tunable paramagnetic tensors are simply obtained in an α-helix that possesses solvent exposed residues in positions i and i + 3, where i is the residue to be mutated to cysteine, i + 3 is Gln or Glu or i - 4 is His. The coordination of a sidechain carboxylate/amide or imidazole to cobalt(II) results in different structural geometries, leading to different paramagnetic tensors as shown by experimental data.

Oxidative Cleavage of Styrenes Catalyzed by a PdIIComplex of an 8-Hydroxyquinolinonate Ligand

Synthesis and catalytic activity of palladium complexes of 8-(pyridin-2-ylmethoxy)quinolinone (3) were investigated. Complexation of 3 with [Pd(CH3CN)2Cl2] gave the dimeric palladium complex [{N,N-(3)PdCl}2] (4). The structure of 4 was characterized by1H/13C NMR spectroscopy and mass spectrometry, and further confirmed by X-ray crystallography. Complex 4 acts as a catalyst for oxidative cleavage of C=C bonds, and it catalyzes the hydration of styrenes in an anti-Markovnikov Wacker manner to give terminal aldehydes as the initial product, which then undergo C–C cleavage to yield the corresponding benzaldehydes. Systematic studies of this catalysis were performed.

HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and neurological disorders, including, but not limited to, e.g., psychosis, schizophrenia, depression, movement disorders, and Parkinson's disease.