15644-91-4

Usage

Uses

Used in Pharmaceutical Industry:
6-Ethoxy-2-methyl-4-quinolinol is used as a potential therapeutic agent for various diseases, including arthritis, Alzheimer's, and cancer, due to its anti-inflammatory, antioxidant, and antimicrobial properties.
Used in Metal Detection and Extraction:
6-Ethoxy-2-methyl-4-quinolinol is used as a chelating agent for metal ions, making it useful in metal detection and extraction processes.
Used in Analytical Chemistry:
6-Ethoxy-2-methyl-4-quinolinol is used as a complexing agent in analytical chemistry, aiding in the analysis and detection of various compounds.
Used in Parasitic Infections Treatment:
6-Ethoxy-2-methyl-4-quinolinol is used as a potential drug for treating parasitic infections, although further research is needed to evaluate its safety and efficacy.

InChI:InChI=1/C12H13NO2/c1-3-15-9-4-5-11-10(7-9)12(14)6-8(2)13-11/h4-7H,3H2,1-2H3,(H,13,14)

Upstream product

• 22015-95-8 ethyl 3-((4-ethoxyphenyl)amino)but-2-enoate 
• 141-97-9 ethyl acetoacetate 
• 156-43-4 4-Ethoxyaniline 
• 920312-63-6 ethyl (Z)-3-(4-ethoxyphenylamino)but-2-enoate 

Downstream Products

• 66735-22-6 4-chloro-6-ethoxy-2-methylquinoline 
• 811412-57-4 6-ethoxy-2-methyl-4-phenoxy-quinoline 
• 1353579-15-3 C₂₃H₂₇NOS 

Relevant academic research and scientific papers

New insights into the SAR and drug combination synergy of 2-(quinolin-4-yloxy)acetamides against Mycobacterium tuberculosis

2-(Quinolin-4-yloxy)acetamides have been described as potent and selective in vitro inhibitors of Mycobacterium tuberculosis (Mtb) growth. Herein, a new series of optimized compounds were found to demonstrate highly potent antitubercular activity, with minimum inhibitory concentration (MIC) values against drug-susceptible and drug-resistant Mycobacterium tuberculosis strains in the submicromolar range. Furthermore, the most active compounds had no apparent toxicity to mammalian cells, and they showed intracellular activities similar to those of isoniazid and rifampin in a macrophage model of Mtb infection. Use of the checkerboard method to investigate the association profiles of lead compounds with first- and second-line antituberculosis drugs showed that 2-(quinolin-4-yloxy)acetamides have a synergistic effect with rifampin. Ultimately, the good permeability, moderate rates of metabolism and low risk of drug-drug interactions displayed by some of the synthesized compounds indicate that 2-(quinolin-4-yloxy)acetamides may yield candidates to use in the development of novel alternative therapeutics for tuberculosis treatment.

Searching for New Leads for Tuberculosis: Design, Synthesis, and Biological Evaluation of Novel 2-Quinolin-4-yloxyacetamides

In this study, a new series of more than 60 quinoline derivatives has been synthesized and evaluated against Mycobacterium tuberculosis (H37Rv). Apart from the SAR exploration around the initial hits, the optimization process focused on the improvement of the physicochemical properties, cytotoxicity, and metabolic stability of the series. The best compounds obtained exhibited MIC values in the low micromolar range, excellent intracellular antimycobacterial activity, and an improved physicochemical profile without cytotoxic effects. Further investigation revealed that the amide bond was the source for the poor blood stability observed, while some of the compounds exhibited hERG affinity. Compound 83 which contains a benzoxazole ring instead of the amide group was found to be a good alternative, with good blood stability and no hERG affinity, providing new opportunities for the series. Overall, the obtained results suggest that further optimization of solubility and microsomal stability of the series could provide a strong lead for a new anti-TB drug development program.

NaHSO4/SiO2: An efficient catalyst for the synthesis of β-enaminones and 2-methylquinolin-4(1H)-ones under solvent-free condition

An efficient and simplified protocol for NaHSO4/SiO2 catalyzed solvent-free synthesis of β-enaminone and 2-methylquinolin-4(1H)- one derivatives under microwave irradiation is described. A series of functionalized derivatives have been synthesized in shorter reaction times with moderate to good yields. The use of milder catalyst in non-conventional method offers significant advantages over conventional methods, such as higher selectivities, simplicity, solvent-free reaction and non-environmental polluting conditions.

Design, synthesis and in vitro antitumor activity of 4-aminoquinoline and 4-aminoquinazoline derivatives targeting EGFR tyrosine kinase

Two series of new 6-alkoxy-4-substituted-aminoquinazolines (2-4f) and their bioisoteric quinoline congeners (5-7c) were designed and synthesized. Virtual screening was carried out through docking the designed compounds into the ATP binding site of epidermal growth factor receptor (EGFR) to predict if these compounds have analogous binding mode to the EGFR inhibitors. The newly synthesized compounds were tested in vitro on human breast carcinoma cell line (MCF-7) in which EGFR is highly expressed. Most of the tested compounds exploited potent antitumor activity with IC50 values in the nanomolar range in particular compound 3b which displayed the highest activity among the tested compounds with IC50 equal to 0.13 nmol.

New 6-ethoxyquinolines as simple optoquine analogues

Reaction of 6-ethoxylepidine (6-ethoxy-4-methylquinoline) with strong base and electrophiles leads to new derivatives, as possible optoquine analogues.