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 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 3281-08-1 8-quinolinoxyacetic acid hydrazide 
• 88349-90-0 ethyl ((5-chloroquinolin-8-yl)oxy)acetate 

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

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.

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

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.

Synthesis of some novel 3,4,5-trisubstituted triazole derivatives bearing quinoline ring and evaluation of their antimicrobial activity

Some new 3,4,5-trisubstituted 1,2,4-triazole derivatives were synthesized and studied for their antimicrobial activity. The lead compounds were obtained starting from 8-hydroxyquinoline and ethyl 2-chloroacetate. The obtained ester compound (1) first reac

New Schiff bases of 2-(quinolin-8-yloxy)acetohydrazide and their Cu(ii), and Zn(ii) metal complexes: Their in vitro antimicrobial potentials and in silico physicochemical and pharmacokinetics properties

The purpose of this work was to prepare Schiff base ligands containing quinoline moiety and using them for preparing Cu(ii) and Zn(ii) complexes. Four bidentate Schiff base ligands (SL1-SL4) with quinoline hydrazine scaffold and a series of mononuclear Cu(ii) and Zn(ii) complexes were successfully prepared and characterized. The in vitro antibacterial and antifungal potential experimentation revealed that the ligands exhibited moderate antibacterial activity against the Gram-positive bacterial types and were inactive against the Gram-negative bacteria and the fungus strains. The metal complexes showed some enhancement in the activity against the Gram-positive bacterial strains and were inactive against the Gram-negative bacteria and the fungus strains similar to the parent ligands. The complex [Cu(SL1)2] was the most toxic compound against both Gram-positive S. aureus and E. faecalis bacteria. The in silico physicochemical investigation revealed that the ligand SL4 showed highest in silico absorption (82.61percent) and the two complexes [Cu(SL4)2] and [Zn(SL4)2] showed highest in silico absorption with 56.23percent for both compounds. The in silico pharmacokinetics predictions showed that the ligands have high gastrointestinal (GI) absorption and the complexes showed low GI absorption. The ligands showed a good bioavailability score of 0.55 where the complexes showed moderate to poor bioavailability.