13788-72-2

Usage

Uses

Used in Pharmaceutical Applications:
4-HYDROXY-6-METHOXYQUINOLINE is used as a pharmaceutical agent for its antimicrobial, antifungal, antioxidant, and anti-inflammatory properties. It can be employed in the development of treatments for various infections and inflammatory conditions due to its broad-spectrum activity against microorganisms and its ability to modulate immune responses.
Used in Industrial Applications:
In the industrial sector, 4-HYDROXY-6-METHOXYQUINOLINE is used as a chelating agent in metal ion coordination chemistry. Its ability to form stable complexes with metal ions makes it a valuable component in various chemical processes and applications, such as catalysis and the synthesis of metal-organic frameworks.
Used in Organic Synthesis:
4-HYDROXY-6-METHOXYQUINOLINE is used as a building block in the synthesis of organic compounds. Its unique structure and functional groups make it a versatile starting material for the creation of a wide range of organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals.
Overall, 4-HYDROXY-6-METHOXYQUINOLINE has demonstrated its potential as a multifunctional chemical with applications in various industries, including pharmaceuticals, industrial chemistry, and organic synthesis. Its diverse properties and uses highlight its importance and value in the development of new products and technologies.

Upstream product

• 25063-43-8 2,2-dimethyl-5-(((4-methoxyphenyl)amino)methylene)-1,3-dioxane-4,6-dione 
• 141-82-2 malonic acid 
• 104-94-9 4-methoxy-aniline 
• 122-51-0 orthoformic acid triethyl ester 
• 22106-39-4 1-(3-methoxy-4-nitrophenyl)ethanone 
• 42887-67-2 1-(5-methoxy-2-nitrophenyl)ethanone 
• 3835-21-0 6-methoxy-2,3-dihydroquinolin-4(1H)-one 
• 7661-29-2 1-(4-methoxyphenyl)-2-azetidinone 
• 696-62-8 para-iodoanisole 
• 83507-70-4 diethyl 2-(((4-methoxyphenyl)amino)methylene)malonate 
• 53976-97-9 ethyl 6-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylate 
• 107-31-3 Methyl formate 
• 23042-77-5 1-(2-amino-5-methoxy-phenyl)-ethanone 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 42881-66-3 4-bromo-6-methoxyquinoline 
• 1283075-20-6 1-benzyloxycarbonyl-6-methoxy-4-quinolone 

Relevant academic research and scientific papers

Gas-phase pyrolysis in organic synthesis: Rapid green synthesis of 4-quinolinones

Gas-phase pyrolysis of aminomethylene Meldrum's acid derivatives gave quinolinones and/or amines depending on the nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate. Georg Thieme Verlag Stuttgart.

Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone

Cobalt(III) and rhodium(III) catalysts exhibited complementary scope in C-H amidation of aryl enaminones. The amidation reactions proceeded with broad scope under the assistance of a weakly coordinating and bifunctional enaminone directing group. The electrophilicity of the enaminone group can be further utilized in subsequent hydrolysis-cyclization reactions to afford NH 4-quinolones in telescoping reactions.

Novel and convenient synthesis of 4(1H)quinolones

A rapid two-step synthesis of 4(1H)quinolones is described. The first step involves condensation of o-nitroacetophenone with N,N-dimethylformamide dimethylacetal yielding highly crystalline enamines. In the second step a reductive cyclization is achieved

Preparation of a resin-bound cyclic malonic ester and a facile solid-phase synthesis of 4(1H)quinolones

A resin-bound cyclic malonic ester has been prepared on Merrifield resin. Reaction of the cyclic malonic ester with triethyl orthoformate and subsequent substitution by an arylamine afforded arylaminomethylene cyclic malonic ester preloaded resin. A serie

Cu(I)-Catalyzed Alkynylation of Quinolones

Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.

Structure-Activity Relationship of Anti-Mycobacterium abscessus Piperidine-4-carboxamides, a New Class of NBTI DNA Gyrase Inhibitors

Mycobacterium abscessus causes difficult-to-cure pulmonary infections. The bacterium is resistant to most anti-infective agents, including first line antituberculosis (anti-TB) drugs. MMV688844 (844) is a piperidine-4-carboxamide (P4C) with bactericidal properties against M. abscessus. We recently identified DNA gyrase as the molecular target of 844. Here, we present in silico docking and genetic evidence suggesting that P4Cs display a similar binding mode to DNA gyrase as gepotidacin. Gepotidacin is a member of the Novel Bacterial Topoisomerase Inhibitors (NBTIs), a new class of nonfluoroquinolone DNA gyrase poisons. Thus, our work suggests that P4Cs present a novel structural subclass of NBTI. We describe structure-activity relationship studies of 844 leading to analogues showing increased antibacterial activity. Selected derivatives were tested for their inhibitory activity against recombinant M. abscessus DNA gyrase. Further optimization of the lead structures led to improved stability in mouse plasma and increased oral bioavailability.

Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors

General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.

COMPOUND, OPTICAL RESOLUTION METHOD, AND DERIVATIVE OF AN OPTICAL ISOMER OF AN AMINO ACID

Disclosed is a compound represented by chemical formula (1): or chemical formula (2):

Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy

A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.

Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels

Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.