15450-76-7

Basic information

• Product Name: 2,8-Quinolinediol
• Synonyms: 2,8-DIHYDROXYQUINOLINE;2,8-DIHYDROQUINOLINE;2,8-QUINOLINEDIOL;8-Hydroxycabostyril;8-HYDROXYCARBOSTYRIL;QUINOLINE-2,8-DIOL;2,8-DIHYDROXY-CHINOLIN;2,8-Dihydroxyquinoleine
• CAS NO: 15450-76-7
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: -0
• Product Categories: Quinolines, Quinazolines and derivatives;Quinoline derivatives;Quinoline&Isoquinoline;Quinolines;Heterocycles;Inhibitors
• Mol File: 15450-76-7.mol

Chemical Properties

• Melting Point: ~290 °C (dec.)
• Boiling Point: 403.2 °C at 760 mmHg
• Flash Point: 197.6 °C
• Appearance: white to crystalline powder
• Density: 1.337 g/cm³
• Vapor Pressure: 4.46E-07mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: Room temperature.
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 8.85±0.20(Predicted)
• BRN: 472906
• CAS DataBase Reference: 2,8-Quinolinediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,8-Quinolinediol(15450-76-7)
• EPA Substance Registry System: 2,8-Quinolinediol(15450-76-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 15450-76-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Compounds:
2,8-Quinolinediol is used as a starting reagent in the preparation of pharmaceutical compounds, particularly due to its quinolone derivative nature.
Used in Toxicity and Pathogenesis Studies:
2,8-Quinolinediol is suitable for use as a standard in studies aimed at identifying urinary metabolites related to toxicity and pathogenesis induced by doxorubicin (DOX) in rats. This application utilizes online and off-line LC-MS techniques to analyze the metabolites.
Used in Asthma Treatment:
2,8-Quinolinediol serves as a starting reagent for the preparation of two potent β2-adrenergic receptor agonists, Procaterol and Indacaterol, which are used for the treatment of asthma. These agonists help in relaxing the smooth muscles of the airways, providing relief from asthma symptoms.
Used in UV-Absorbing Compounds:
As a detected new UV-absorbing compound (UAC) in cow milk, 2,8-Quinolinediol may have potential applications in the development of materials or products that require UV absorption properties, such as sunscreens or protective coatings.

InChI:InChI=1/C9H7NO2/c11-7-3-1-2-6-4-5-8(12)10-9(6)7/h1-5,11H,(H,10,12)

Upstream product

• 148-24-3 8-quinolinol 
• 84-88-8 8-quinolinol-5-sulfonic acid 
• 15450-72-3 2-hydroxyquinolin-8-yl acetate 
• 22614-69-3 8-methoxy-1H-quinolin-2-one 
• 77432-37-2 o-(3-ethoxyacryloylamino)phenol 
• 15450-72-3 2-oxo-1,2-dihydroquinolin-8-yl acetate 
• 6889-84-5 N-(2-methoxyphenyl)-3-phenylacrylamide 
• 15851-89-5 (E)-p-methylcinnamoyl chloride 
• 1866-39-3 trans-p-methylcinnamic acid 
• 39856-08-1 (E)-3,4-dimethoxycinnamic chloride 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 95-55-6 2-amino-phenol 
• 77432-38-3 N-(3,3-di-n-butoxypropionyl)-o-anisidine 
• 77432-36-1 N-(3-ethoxyacryloyl)-o-anisidine 

Downstream Products

• 15450-72-3 2-hydroxyquinolin-8-yl acetate 
• 31568-91-9 2-chloroquinolin-8-ol 
• 15450-73-4 2,5,8(1H)-quinolinetrione 
• 193821-72-6 8-(2-Biphenyl-4-yl-2-oxo-ethoxy)-1H-quinolin-2-one 
• 193821-68-0 8-(2-Oxo-2-phenyl-ethoxy)-1H-quinolin-2-one 

Relevant articles and documents

Kinetics of procaterol auto-oxidation in buffered acid solutions

The kinetics of procaterol (1) degradaton in buffered acidic solutions (pH 4-6) was investigated using a HPLC procedure. The effect of temperature and ferric ions on the reaction rate was estimated. In acidic solutions, 1 undergoes pseudo first-order degradation with an induction period. The first-order rate constant for degradation increased and the induction period decreased with an increase in pH. Ferric ions catalyzed the degradation reaction and decreased the induction period. At pH 6, the activation energy of the reaction was 34.5 kcal/mol/deg. The results of this study indicate that 1 in solution is more stable at acidic pH, in the absence of heavy metal ions, and protected from air.

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.

Preparation method of indacaterol intermediate 5-chloracetyl-8-benzyloxy-2(1H)-quinolinone

The invention discloses a preparation method of an indacaterol intermediate 5-chloracetyl-8-benzyloxy-2(1H)-quinolinone. The method includes: taking o-methoxyaniline, cinnamoyl chloride, aluminium trichloride, trifluoromethanesulfonic acid, chloroacetyl chloride, and benzyl bromide as the raw materials, and carrying out four-step reaction, i.e. amidation reaction, ring closing reaction, Friedel-Crafts reaction, and hydroxylation reaction. The preparation method provided by the invention has the advantages of high yield, low cost, few three waste, easy operation and safety, and is suitable forindustrialization.

Method for preparing hydroxyl-2(1H)-quinolinone

The invention discloses a method for preparing hydroxyl-2(1H)-quinolinone, and belongs to the field of organic chemistry. The method comprises the following steps: enabling an aminophenylboric acid compound and trans-beta-aryl acryloyl chloride to react under the existence of triethylamine or pyridine so as to generate a trans-amide intermediate, and then carrying out temperature rising reaction in an organic solvent under the existence of aluminum chloride anhydrous and B(C6F5)3; cooling after completing the reaction, and adding hydrogen peroxide for oxidization, thus obtaining the hydroxyl-2(1H)-quinolinone. The method disclosed by the invention has the advantages that raw materials are easy to obtain, hydroxyl quinolinone products in different positions can be obtained through differentinitial raw materials, and an existing synthetic route is enriched.

Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes

Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.

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.

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.

Sulfonamide peri-substituted bicyclics for occlusive artery disease

Acyl sulfonamide, peri-substituted, fused bicyclic ring compounds useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed. The compounds are of the general formula A representative example is:

NOVEL COMPOUNDS

The invention provides compounds of formula (I) wherein m, R1, n, R2, q, X, Y, R3, R4, R5, R6, R7 and R8 are as defined in the specification, processes for their prepa

NOVEL TRICYCLIC SPIRODERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The invention provides compounds of formula (I) wherein m, R1, n, R2, q, p, X, Y, R3, R4, t and, R5 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.