75457-13-5

Usage

Uses

Used in Biophysical Probes:
3-Methyl-8-hydroxyquinoline is used as an intermediate in the synthesis of metal-ion chelating amino acids, which are incorporated into proteins to act as biophysical probes. This application allows researchers to study the structure, function, and dynamics of proteins in various biological systems.
Used in Chemical Synthesis:
3-Methyl-8-hydroxyquinoline is utilized as a key component in the synthesis of various organic compounds, including pharmaceuticals, dyes, and other specialty chemicals. Its unique structure and reactivity make it a valuable building block in the development of new and innovative products.

Upstream product

• 50-00-0 formaldehyd 
• 123-38-6 propionaldehyde 
• 95-55-6 2-amino-phenol 
• 78-85-3 2-methylpropenal 
• 90-04-0 2-methoxy-phenylamine 
• 112955-06-3 8-methoxy-3-methylquinoline 
• 1004545-97-4 2-amino-3-hydroxybenzaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 
• 42123-33-1 3-hydroxy-2-nitrobenzaldehyde 

Downstream Products

• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 3393-71-3 3-methyl-[8]quinolylamine 

Relevant academic research and scientific papers

Controlling the helicity of hydroxyquinoline metal complexes based on a macrocyclic peptide scaffold

A straightforward synthesis of a C3-symmetric imidazolecontaining macrocyclic peptide with three hydroxyquinoline side arms is presented. Complex formation with various metal ions (Al3+, Ga 3+, Fe3+, La3+ and Y3+) was investigated by spectrophotometry methods. CD spectroscopy revealed a highly diastereoselective binding of these ions at: room, temperature. In the case of Al3+, Ga3+ and La3+ complexes, Job plot analyses gave evidence of pure 1:1 stoichiometry. Ab initio calculations for the Al3+ and Ga3+ complexes showed that the A isomers are considerably stabilized relative to the A isomers, Furthermore, the calculated CD spectra for the Al3+ complexes confirm the formation of the A isomers in solution. 2009 Wiley-VCH Verlag GmbH & Co. KGaA,.

Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes

Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.

Microwave-enhanced Friedl?nder synthesis for the rapid assembly of halogenated quinolines with antibacterial and biofilm eradication activities against drug resistant and tolerant bacteria

Herein, we disclose the development of a catalyst- and protecting-group-free microwave-enhanced Friedl?nder synthesis which permits the single-step, convergent assembly of diverse 8-hydroxyquinolines with greatly improved reaction yields over traditional oil bath heating (increased from 34% to 72%). This rapid synthesis permitted the discovery of novel biofilm-eradicating halogenated quinolines (MBECs = 1.0-23.5 μM) active against MRSA, MRSE, and VRE. These small molecules exhibit activity through mechanisms independent of membrane lysis, further demonstrating their potential as a clinically useful treatment option against persistent biofilm-associated infections.

Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalisation of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biologically active compounds.

Novel Sulfonaminoquinoline Hepcidin Antagonists

The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.

Method for the preparation of pyridine-2,3-dicarboxylic acids

The present invention provides an improved method for the preparation of pyridine-2,3-dicarboxylic acids by the continuous oxidation of substituted quinolines.

Synthesis of mono-and dialkylsubstituted 1,10-Phenanthrolines

Starting from o-anisidine, alkylated 8-hydroxyquinolines 2 and 8-aminoquinolines 3 were obtained. From the latter, dialkylsubstituted 1,10-phenanthrolines 5 have been prepared in good yields. Reaction of unsubstituted 8-aminoquinoline under the same conditions, yielded monoalkylated 1,10-phenanthrolines 4.

Method for the preparation of pyridine-2,3-dicarboxylic acids

The present invention provides a novel method for the preparation of pyridine-2,3-dicarboxylic acids by the oxidation of 8-substituted quinolines.