1571-30-8

Usage

Uses

Used in Chemical Synthesis:
8-Hydroxy-2-quinolinecarboxylic acid is used as a chelating agent for the preparation of bis(8-hydroxyquinoline-2-carboxylato-Κ3N,O,O′) cobalt (II) trihydrate. This application takes advantage of its ability to form stable complexes with metal ions, which is useful in various chemical reactions and the synthesis of coordination compounds.
Used in Analytical Chemistry:
8HQC is used as a reagent in the development of a probe for detecting water in aprotic organic solvents. Its fluorescence quenching property upon reaction with water makes it a valuable tool in analytical chemistry for monitoring the presence of water in various organic solvents, which is crucial for maintaining the purity and reactivity of these solvents in chemical processes.
Used in Pharmaceutical Industry:
8-Hydroxy-2-quinolinecarboxylic acid may also find applications in the pharmaceutical industry, particularly in the development of new drugs or drug delivery systems. Its chelating properties and potential for forming various tautomers could be exploited to design novel drug molecules with specific therapeutic properties or to enhance the solubility and bioavailability of existing drugs.
Used in Material Science:
The unique chemical properties of 8HQC, such as its ability to form stable complexes with metal ions and its fluorescence quenching behavior, may also be useful in material science. It could be employed in the development of new materials with specific optical, electronic, or magnetic properties, or as a component in the synthesis of advanced materials for various applications, such as sensors, catalysts, or energy storage devices.

InChI:InChI=1/C10H7NO3/c12-8-3-1-2-6-4-5-7(10(13)14)11-9(6)8/h1-5,12H,(H,13,14)/p-1

Upstream product

• 78224-64-3 (E)-8-methoxy-2-styrylquinoline 
• 95-55-6 2-amino-phenol 
• 14510-06-6 2-formyl oxine 
• 148-24-3 8-quinolinol 
• 88-75-5 2-hydroxynitrobenzene 
• 90-04-0 2-methoxy-phenylamine 
• 7101-82-8 dimethyl 2-((2-methoxyphenyl)amino)but-2-enedioate 
• 4008-46-2 methyl 4-hydroxy-8-methoxyquinoline-2-carboxylate 
• 59-00-7 xanthurenic acid 
• 6686-05-1 C₁₀H₁₀NO₂⁽¹⁺⁾*CH₃O₄S^(1-) 
• 1127-45-3 8-Hydroxyquinoline-N-oxide 
• 3033-80-5 8-methoxy-2-methylquinoline 
• 826-81-3 2-methyl-8-quinolinol 
• 6759-78-0 8-hydroxyquinoline-2-carbonitrile 

Downstream Products

• 21638-90-4 methyl 8-hydroxyquinoline-2-carboxylate 
• 1185410-62-1 rac-2-(benzyloxycarbonyl-amino)-3-[(8-trifluoromethanesulfonyloxy-quinoline-2-carbonyl)amino]propionic acid methyl ester 
• 1072830-83-1 8-hydroxy-quinoline-2-carboxylic acid benzyl ester 
• 1357357-56-2 8-hydroxy-N-phenylquinoline-2-carboxamide 

Relevant academic research and scientific papers

Oriented crystallization of CuSO4·5H2O under a monolayer of a novel amphiphilic ligand, 8-hexadecyloxyquinaldic acid

A new amphiphilic ligand, 8-hexadecyloxyquinaldic acid (HQA), has been synthesized and the characteristics of its monolayer on pure water and on CuSO4 aqueous solution have been examined. The HQA monolayer can interact with copper ions in the subphase, and crystallization of CuSO4·5H2O is induced under the monolayer. In order to understand the relationship between the different states of the monolayer and the induced inorganic crystallization, several typical states of the monolayer were chosen in our experiment. The results show that, when the monolayer is in the gas or liquid phase, its ability to control the oriented crystallization is poor. However, rather than the most dense phase, the most favorable state for oriented crystallization is the one with an area per molecule A = 17.0 A2, which could be considered as a liquid solid phase. This is attributed to a coordination effect and lattice matching at the inorganic/organic interface. Our research suggests that the state of the monolayer is a very important factor during the process of induced oriented crystallization.

Preparation and characterization of Langmuir-Blodgett films of N-hexadecyl-8-hydroxy-2-quinolinecarboxamide and its lanthanum complex

A new amphiphilic ligand, N-hexadecyl-8-hydroxy-2-quinolinecarboxamide (HHQ), and its lanthanum complex La(HHQ)2, were synthesized and characterized by elemental analysis, IR and 1H NMR spectroscopy. The characteristics of the monolayer, Langmuir-Blodgett (LB) films and cast films of HHQ and La(HHQ)2 were investigated by different physical methods, including surface pressure-area isotherms, absorption and fluorescence spectra and low-angle X-ray diffraction analysis. The LB film of La(HHQ)2 has good vertical homogeneity and the in-plane conductivity parallel to the compression direction is found to be 3.85 × 10-5 Sm-1.

Synthesis, spectroscopy and computational studies of selected hydroxyquinoline carboxylic acids and their selected fluoro-, thio-, and dithioanalogues

The faster and more efficient new synthetic methodologies of crystalline hydroxyquinoline carboxylic acids and their fluoro-, thio- and dithioanalogues were elaborated. The FTIR, multinuclear NMR, UV-Vis and single crystal X-ray characteristics of the series of quinoline carboxylic acids have been determined experimentally and rationalized on the basis of DFT calculation method with B3LYP functional.

Nitric oxide-donating and reactive oxygen species-responsive prochelators based on 8-hydroxyquinoline as anticancer agents

Metal ion chelators based on 8-hydroxyquinoline (8-HQ) have been widely explored for the treatment of many diseases. When aimed at being developed into potent anticancer agent, a largely unmet issue is how to avoid nonspecific chelation of metal ions by 8

Fluorescent schiff base probes for sequential detection of Al3+ and F? and cell imaging applications

Two novel Schiff-base fluorescent probers SQ and NQ based on 8-hydroxyquinoline moiety were designed and synthesized. The both probes were capable of binding with Al3+ by naked eye detection to produce a significant fluorescence enhancement response with a detection limit of 1.48 × 10?8 and 4.23 × 10?8 M, respectively. At the same time, the formed complexes SQ-Al3+ and NQ-Al3+ could sequentially detect F?, and the detection limits of F? were determined to be 1.64 × 10?7 and 3.58 × 10?8 M, respectively. The “off-on-off” fluorescence response process demonstrated that the binding were reversible. The probes were further successfully utilized to detect Al3+ and F? in vitro PC12 cells.

Quinoline tryptamine heterozygote and application thereof in preparation of medicines for treating Alzheimer's disease

The invention belongs to the technical field of medicines, and particularly relates to a quinoline tryptamine heterozygote and application thereof in preparation of medicines for treating and/or preventing Alzheimer's disease. Specifically disclosed are a compound represented by formula (I) and a pharmaceutically acceptable salt thereof. The quinoline tryptamine heterozygote disclosed by the invention has excellent oxygen free radical scavenging capacity, a protective effect on hydrogen peroxide induced SH-SY5Y cell oxidative damage, good blood-brain barrier passive dialysis capacity, an A[beta] self-aggregation inhibiting effect and metal ion chelating capacity, and is a multi-target anti-Alzheimer disease active molecule. The compound is expected to be used as a clinical medicine for treating and/or preventing Alzheimer's disease.

Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide

A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).

Synthesis and biological evaluation of novel 8-substituted quinoline-2-carboxamides as carbonic anhydrase inhibitors

A series of novel 8-substituted-N-(4-sulfamoylphenyl)quinoline-2-carboxamides was synthesised by the reaction of 8-hydroxy-N-(4-sulfamoylphenyl) quinoline-2-carboxamide with alkyl and benzyl halides. The compounds were assayed for carbonic anhydrase (CA)

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.