42322-30-5

Usage

Synthesis

To a solution of 8-hydroxy quinoline (0.5 mole) in dry acetone (150 mL), ethyl chloroacetate (0.60 mole) were added followed by anhydrous K2CO3 (1.0 mole). After reflux for 20 hour the solvent was removed and the reaction mixture was treated with water, extracted with benzene several times and the collected organic layer was dried on anhydrous Na2SO4, filtered and evaporated to give Ethyl (quinolin-8-yloxy) acetate(AKOS AU36-M554).

Upstream product

• 148-24-3 8-quinolinol 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 73511-58-7 4-phenyl-5-[((quinolin-8-yloxy)methyl)-4H-1,2,4-triazole-3-thiol] 
• 73511-70-3 2-((4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl)thio) acetic acid 

Relevant academic research and scientific papers

Facile synthesis of tricyclic oxazino- or oxazepino-fused tetrahydroquinolines via intramolecular reductive amidation

Reductive cyclization of -(8-quinolyloxy)alkyl esters by zinc in acetic acid is shown to constitute a convenient methodology for the synthesis of oxazino- or oxazepino-fused tetrahydroquinolines. It is operationally simple, requires a short reaction time, and provides excellent yields. Georg Thieme Verlag Stuttgart ? New York.

A newly synthesized sulphated 8-hydroxyquinoline derivative to effectively control aluminum corrosion in perchloric acid: Electrochemical and positron annihilation studies

The corrosion of aluminum in 1.0 M HClO4 was effectively controlled by a newly synthesized sulphated 8-hydroxy-quinoline derivative (8HQD), namely 2-(2-(quinolin-8-yloxy)acetamido)ethyl hydrogen sulfate. Rates of corrosion were monitored as a function of C8HQD (C8HQD: 10- 4-10- 2 M) using Tafel extrapolation method and linear polarization resistance (LPR) measurements. The electron density and corrosion-related defects in corroded and inhibited Al samples were probed using the positron annihilation lifetime (PAL) and positron annihilation Doppler broadening (PADB) techniques. Results were compared with 8-hydroxyquinoline (8HQ) itself. Polarization studies indicated that 8HQD acted as a mixed-type inhibitor with anodic predominance. PAS measurements demonstrated that the PAL components (τi) and their corresponding intensities (Ii) as well as PADB line-shape parameters (S and W) can be used to assess the inhibition performance of the tested materials. Results obtained from the different corrosion evaluation techniques were in good agreement and went parallel with those of PAS measurements. 8HQD was much better than 8HQ in inhibiting Al corrosion in these solutions.

A smart molecular probe for selective recognition of nitric oxide in 100% aqueous solution with cell imaging application and DFT studies

Herein, a simple, least-cytotoxic as well as an efficient fluorescent sensor HqEN480 was prepared from (quinolin-8-yloxy)-acetic acid ethyl ester (L1) and N,N-dimethylethylene diamine to recognize NO in 100% aqueous solution. Its marked selectivity and sensitivity towards NO, makes it a highly suitable probe for nitric oxide under in vitro conditions with the possibility of in vivo monitoring of NO. Upon addition of 3.5 equivalents of NO, there is an approximately 7 fold enhancement in fluorescence intensity in aqueous solution with a corresponding Kf value of (1.75 ± 0.07) × 104 M-1. Quantum yields of HqEN480 and [HqEN480-NO] compounds are determined to be 0.04 and 0.22, respectively, using acidic quinine sulphate as a standard. In terms of the 3σ method, the LOD for nitric oxide was found to be 53 nM thus, making the probe suitable for tracking NO in biological systems.

Synthesis, structure analysis, DFT calculations and energy frameworks of new coumarin appended oxadiazoles, to regress ascites malignancy by targeting VEGF mediated angiogenesis

Ascites malignancy is a frequent cause of morbidity and presents significant management problems which occur in many cancers. Angiogenesis plays a major role in the prognosis of ascites tumor through Vascular Endothelial Growth Factor (VEGF). Inhibition o

Fluorescence sensor based on quinoline derivative, synthesis of fluorescence sensor and application of fluorescence sensor in detection of aluminum ions

The invention designs and synthesizes a fluorescence sensor based on a quinoline derivative, which is prepared by the following steps of: taking 8-hydroxyquinoline and 2-ethyl bromoacetate as substrates, and reacting in an acetonitrile solvent to prepare

Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies

A series of caffeic acid (CA) derivatives 7a-j were synthesized via etherification and coupling action and their chemical structures were elucidated spectroscopically. Motivated by the various biological activities displayed by CA derivatives such as anti-inflammatory, antiviral, anticancer and antioxidant and also based on its extensively consumption in the human diet. In the present work, the newly synthesized compounds 7a-j were evaluated for anti-inflammatory and analgesic action and most of them exerted comparable activity to the reference compound celecoxib. Further, ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drug. Among the title series 7a-j, compounds 7f and 7g with electron withdrawing bromo and chloro group respectively, at the para position of the phenoxy ring was showed good activity compared to all other compounds. Interestingly, the COX-I/COX-II activity ratio of potent compounds 7f and7g showed an almost equal inhibitory effect on both isoenzymes. Further, molecular docking studies have been performed for the potent compounds which showed statistically significant result.

A New Series of 1,3,4-Oxadiazole Linked Quinolinyl-Pyrazole/Isoxazole Derivatives: Synthesis and Biological Activity Evaluation

Abstract: A series of 1,3,4-oxadiazole bridged pyrazole/isoxazole bearing quinoline derivatives has been designed and synthesized by a clean and convenient method. Structures of the newly synthesized compounds have been confirmed by FTIR, 1H and 13C NMR, and HRMS spectral data. The titled compounds have been evaluated for their molecular docking guided antimicrobial and anti-inflammatory activity. One of 1,3,4-oxadiazole bridged quinolinyl-pyrazole derivatives has interacted efficiently with E. Coli protein (PDB file: 1KZN), and has been characterized by good antimicrobial activity against the majority of the tested pathogens. Another product has exhibited excellent anti-inflammatory activity.

A facile AIE fluorescent probe for broad range of pH detection

Detection of pH has received more and more attention in various fields. Currently, a hot research topic is focused on how to use a facile fluorescent dye to achieve a wide range and accurate pH detection. Herein, we reported a simple fluorescence probe for pH detection with wide range and accuracy based on the Aggregation-Induced Emission (AIE) characteristics. The probe 2-oxo-N’-(2-(quinolin-8-yloxy)acetyl)-2H-chromene-3-carbo- hydrazide (CHBQ) as comprised of coumarin and quinoline as the electron donor and acceptor, N, N′-diformylhydrazine bond as the linking group, respectively. The probe displays good AIE characteristics under water content up to 99% in mixed medium. Furthermore, it can identify acid and base as fast as 30 s by color change of the solution under UV365 nm lamp. The detection of the probe for pH was hardly interfered with other ions. What's more, the probe CHBQ can be designed to be a broad range test paper of pH detection, which has a great practical value.

Synthesis, crystal structure, Hirshfeld surface analysis, spectral characterization, reduced density gradient and nonlinear optical investigation on (E)-N'-(4-nitrobenzylidene)-2-(quinolin-8-yloxy) acetohydrazide monohydrate: A combined experimental and DFT approach

In this work, (E)-N'-(4-nitrobenzylidene)-2-(quinolin-8-yloxy) acetohydrazide monohydrate (NBQA) crystal was synthesized and its structural characterization was carried out by single-crystal X-ray diffraction. The intermolecular interactions in the crystal were investigated through the Hirshfeld surface analysis and the 2D-fingerprint plot. In the solid phase, the spectroscopic characterization was also carried out using FT-IR, 1H NMR, and 13C NMR experimental spectroscopies. To support experimental results, DFT calculations have been accomplished on the NBQA molecule in the ground state. First, theoretical calculations were performed using BPV86 and GGA-PBE functionals with the 6-311G(d,p) basis set to obtain the stable conformer of the molecule. Likewise, harmonic vibrational frequencies, 1H and 13C chemical shifts, and NBO analysis were also calculated using the same level of theory and compared to available experimental data. Furthermore, the molecular electrostatic potential (MEP), frontier molecular orbitals (FMO) analysis, HOMO-LUMO energies, energy band gap, density of state (DOS), global chemical reactivity descriptors, and some thermodynamic functions were studied and discussed. UV–Vis spectrum was predicted by the TD-DFT method in chloroform solvent and compared with the experimental spectrum for displaying the involved electronic transitions in the compound. The repulsive, attractive, and Van der Waals strong and weak interactions in NBQA were investigated via the RDG analysis. The NLO properties of NBQA have also investigated in different available solvents by DFT and compared to the most important compounds in the field. The first hyperpolarizability values of NBQA have been increased with increasing solvent polarity and decreasing the energy band gap.

Two similar Schiff-base receptor based quinoline derivate: Highly selective fluorescent probe for Zn(II)

As is known, Zn2+ plays a vital role in a variety of biological processes but excessive exposure of Zn2+ to human beings can cause toxicity, inducing a series of overt poisoning symptoms and neurodegenerative disorders. Thus, we designed and synthesized two quinoline-derived Schiff-bases HL1 and HL2, and investigated the fluorescence emission responses of these two Schiff-bases to various metal ions. A significant enhancement in fluorescence emission band centered at 450 nm was observed in the ethanolic solution of HL1 with addition of Zn2+, while remarkably lower fluorescence emission enhancement was obtained in the case of HL2 in which one methyl group was introduced to the azomethine carbon. In addition, HL1 showed good selectivity and high sensitivity towards Zn2+ in the existence of other various interfering metal ions, and the reversibility and regeneration of HL1 were also perfect for extending its applications in environmental and biological systems. Therefore, HL1 could be identified as a fluorescent probe for sensing Zn2+ environmentally and biologically.