139549-06-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Methoxy-quinoline-3-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its chemical structure allows for the creation of new drug molecules with potential therapeutic applications.
Used as a Reagent in Chemical Reactions:
In the field of chemistry, 2-Methoxy-quinoline-3-carbaldehyde serves as a valuable reagent, facilitating specific chemical reactions and processes that require its unique properties.
Used as a Fluorescent Dye:
2-Methoxy-quinoline-3-carbaldehyde is utilized as a fluorescent dye in various applications, including biological imaging and detection, where its optical properties allow for the visualization and tracking of specific targets.
Used in Material Science for Optoelectronic Devices:
In the material science industry, 2-Methoxy-quinoline-3-carbaldehyde is employed in the development of optoelectronic devices, such as solar cells and light-emitting diodes, due to its light-emitting and light-absorbing characteristics.
Used in Material Science for Sensor Development:
Furthermore, 2-Methoxy-quinoline-3-carbaldehyde has potential applications in the development of sensors, where its chemical reactivity and sensitivity to environmental changes can be harnessed for detecting specific substances or conditions.

InChI:InChI=1/C11H9NO2/c1-14-11-9(7-13)6-8-4-2-3-5-10(8)12-11/h2-7H,1H3

Upstream product

• 67-56-1 methanol 
• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 
• 851777-21-4 methyl 3-[2-hydroxy-2-(2-methoxyquinolin-3-yl)ethyl]-4-nitrobenzoate 
• 1250257-48-7 3-[1,3-dioxolane-2-yl]-2-methoxy-quinoline 
• 103-84-4 Acetanilid 
• 124-41-4 sodium methylate 
• 62-53-3 aniline 

Downstream Products

• 796854-51-8 2-[5-(4-methanesulfonyl-piperazin-1-yl-methyl)-2-nitrophenyl]-1-(2-methoxyquinolin-3-yl)-ethanol 
• 796854-70-1 1-(2-methoxyquinolin-3-yl)-2-(5-methyl-2-nitrophenyl)ethanol 
• 629643-44-3 acetic acid 3-[2-hydroxy-2-(2-methoxy-quinolin-3-yl)-ethyl]-4-nitro-benzyl ester 
• 1329423-64-4 C₁₉H₁₅NO₃ 

Relevant academic research and scientific papers

Facile synthesis of 1-hydroxy-5-methoxy-benzo[f][2,7]naphthyridines

A new route for the synthesis of 1-hydroxy-5-methoxy-benzo[f][2,7] naphthyridines has been developed from easily available precursor 2-chloro-3-formyl quinolines. The 2-methoxy-3-formyl quinolines were prepared and condensed with glycine ethyl ester hydrochloride. This resulted in the formation of an imines, which on cyclization with Dowtherm A yielded 1-hydroxy-5-methoxy-1,2-dihydrobenzo[f][2,7]naphthyridines.

Synthesis of 2-methoxy-3-(thiophen-2-ylmethyl)quinoline containing amino carbinols as antitubercular agents

We have designed and synthesized 2-methoxy-3-(thiophen-2-ylmethyl)quinoline containing amino carbinols as possible anti-tubercular agents to combat the disease. These molecules were synthesized by tethering amino ether linkage with hydroxyl group to diarylquinoline skeleton; hydroxyl and amine chains were engrafted on diaryl ring. They were evaluated against strain (H37Ra) of Mycobacterium tuberculosis and most of compounds showed in vitro antitubercular activity. Two compounds having diaryl quinoline hydroxyl amino ether scaffold and three compounds having diaryl amino alkyl carbinol core showed activities at 6.25 μg/mL. This study explores diaryl carbinol prototype as inhibitor against Mycobacterium tuberculosis.

Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents

A series of novel quinoline-oxadiazole hybrid compounds was designed based on stepwise rational modification of the lead molecules reported previously, in order to enhance bioactivity and improve druglikeness. The hybrid compounds synthesized were screened for biological activity against Mycobacterium tuberculosis H37Rv and for cytotoxicity in HepG2 cell line. Several of the hits exhibited good to excellent anti-tuberculosis activity and selectivity, especially compounds 12m, 12o and 12p, showed minimum inhibitory concentration values 500. The results of this study open up a promising avenue that may lead to the discovery of a new class of anti-tuberculosis agents.

Rational drug design based synthesis of novel arylquinolines as anti-tuberculosis agents

A series of novel arylquinoline derivatives was designed retaining significant pharmacophoric features and three dimensional geometry of bedaquiline. In silico ADME study was performed to assess drug likeness and toxicity profiles of the designed molecules. The compounds were evaluated for activity against Mycobacterium tuberculosis H37Rv using Resazurin Microtitre Assay (REMA) plate method and cytotoxicity in VERO C1008 cell line. Several of the synthesized compounds exhibited good antituberculosis activity and selectivity, especially compounds, 12i (MIC: 5.18 μM and MIC/CC 50: 152.86) and 12l (MIC: 5.59 μM and MIC/CC50: 160.57). The study opens up a new platform for the development of arylquinoline based drugs for treating tuberculosis.

Synthesis and photophysical properties of chiral dendrimers with quinoline surface group via click chemistry

Synthesis of some novel chiral dendrimers containing quinoline as surface group and 1,2,3-triazole as branching unit is described. The chiroptical property exhibits the widening of the torsional angle in the BINOL core as the generation increases. The photophysical properties indicate an increase in the molar extinction coefficient and fluorescence intensity and a decrease in quantum yield and lifetime as the generation of the dendrimer increases.

3-vinylquinolines as cancer cells inhibitors

3-vinylquinolines analogs and methods of synthesizing the derivatives/analogs are provided. In particular, the compounds are useful for the treatment of cancer.

Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents

Several classes of antimalarial drugs are currently available, although issues of toxicity and the emergence of drug resistant malaria parasites have reduced their overall therapeutic efficiency. Quinoline based antiplasmodial drugs have unequivocally been long-established and continue to inspire the design of new antimalarial agents. Herein, a series of mono- and bisquinoline methanamine derivatives were synthesised through sequential steps; Vilsmeier-Haack, reductive amination, and nucleophilic substitution, and obtained in low to excellent yields. The resulting compounds were investigated for in vitro antiplasmodial activity against the 3D7 chloroquine-sensitive strain of Plasmodium falciparum, and compounds 40 and 59 emerged as the most promising with IC50 values of 0.23 and 0.93 μM, respectively. The most promising compounds were also evaluated in silico by molecular docking protocols for binding affinity to the {0 0 1} fast-growing face of a hemozoin crystal model.

Discovery of novel quinoline-based analogues of combretastatin A-4 as tubulin polymerisation inhibitors with apoptosis inducing activity and potent anticancer effect

A new series of quinoline derivatives of combretastatin A-4 have been designed, synthesised and demonstrated as tubulin polymerisation inhibitors. These novel compounds showed significant antiproliferative activities, among them, 12c exhibited the most potent inhibitory activity against different cancer cell lines (MCF-7, HL-60, HCT-116 and HeLa) with IC50 ranging from 0.010 to 0.042 μM, and with selectivity profile against MCF-10A non-cancer cells. Further mechanistic studies suggest that 12c can inhibit tubulin polymerisation and cell migration, leading to G2/M phase arrest. Besides, 12c induces apoptosis via a mitochondrial-dependant apoptosis pathway and caused reactive oxygen stress generation in MCF-7 cells. These results provide guidance for further rational development of potent tubulin polymerisation inhibitors for the treatment of cancer.Highlights A novel series of quinoline derivatives of combretastatin A-4 have been designed and synthesised. Compound 12c showed significant antiproliferative activities against different cancer cell lines. Compound 12c effectively inhibited tubulin polymerisation and competed with [3H] colchicine in binding to tubulin. Compound 12c arrested the cell cycle at G2/M phase, effectively inducing apoptosis and inhibition of cell migration.

Arylquinolinecarboxamides: Synthesis, in vitro and in silico studies against Mycobacterium tuberculosis

A series of fourteen 6-substituted-2-(methoxyquinolin-3-yl) methyl)-N-(pyridin-3-ylmethyl) benzamides was prepared from commercially available anilines in five simple and convenient synthetic steps. The structures of all new products were confirmed by routine spectroscopic methods: IR, 1H and 13C NMR, and HRMS (electrospray ionization). The resulting arylquinolinecarboxamides were subjected to biological screening assay for in vitro inhibitory activity against Mycobacterium tuberculosis (Mtb) H37Rv strain. Several compounds exhibited modest antitubercular activity with compounds 8–11, 15 and 19 exhibiting MIC90 values in the range of 32–85 μM. The antitubercular data suggested that inhibition of Mtb can be imparted by the introduction of a non-polar substituent on C-6 of the quinoline scaffold. Further, to understand the possible mode of action of the series, the reported compounds and bedaquiline were subjected to in silico docking studies against MtbATPase to determine their potential to interfere with the mycobacterial adenosine triphosphate (ATP) synthase. The results showed that these compounds have the potential to serve as antimycobacterial agents. In silico ADME pharmacokinetic prediction results showed the ability of these arylquinolinecarcboxamides to be absorbed, distributed, metabolized and excreted efficiently.

Synthesis, in silico Molecular Docking and Antimicrobial Study of Some New 3-(Substituted-quinolin-3-yl)-1-[4-(1H-pyrrol-1-yl)phenyl]prop-2-en-1-one Derivatives

New series of 3-(substituted-2-chloroquinolin-3-yl)-1-(4-(1H-pyrrol-1-yl)phenyl)prop-2-en-1-ones 4(a-e)/3-(substituted-2-methoxyquinolin-3-yl)-1-(4-(1H-pyrrol-1-yl)phenyl)prop-2-en-1-ones 6(a-e) were synthesized by base catalyzed reaction/chalcone synthes