50741-69-0

Basic information

• Product Name: 4H-Pyran-4-one, 2-ethyl-3-methoxy-
• CAS NO: 50741-69-0
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Mol File: 50741-69-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4H-Pyran-4-one, 2-ethyl-3-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyran-4-one, 2-ethyl-3-methoxy-(50741-69-0)
• EPA Substance Registry System: 4H-Pyran-4-one, 2-ethyl-3-methoxy-(50741-69-0)

Safety Data

• Hazardous Substances Data: 50741-69-0(Hazardous Substances Data)

Usage

Classification

Heterocyclic organic compound belonging to the pyranones class

Main applications

Flavor and fragrance industry, production of pharmaceuticals, intermediate in organic synthesis

Upstream product

• 4940-11-8 2-ethyl-3-hydroxy-4-pyranone 
• 74-88-4 methyl iodide 
• 111782-87-7 3-(benzyloxy)-2-ethyl-4H-pyran-4-one 

Downstream Products

• 1436415-49-4 methyl 2-(6-ethyl-5-methoxy-4-oxo-4H-pyran-3-carbonyl)-3,5-dimethoxybenzoate 

Relevant articles and documents

Dual-target anti-Alzheimer’s disease agents with both iron ion chelating and monoamine oxidase-B inhibitory activity

MAO-B leads to an increase in the levels of hydrogen peroxide and oxidative free radicals, which contribute to the aetiology of the AD. Thus, both iron ion chelators and MAO-B inhibitors can be used to treat AD. Taking the coumarin derivatives and hydroxypyridinones as the lead compounds, a series of dual-target hybrids were designed and synthesised by Click Chemistry. The compounds were biologically evaluated for their iron ion chelating and MAO-B inhibitory activity. Most of the compounds displayed excellent iron ion chelating activity and moderate to good anti-MAO-B activity. Compounds 27b and 27j exhibited the most potent MAO-B inhibitory activity, with IC50 values of 0.68 and 0.86 μM, respectively. In summary, these dual-target compounds have the potential anti-AD activity.

Synthetic method for amino-containing hydroxypyridone compound

The invention discloses a synthetic method for an amino-containing 3-hydroxypyridine-4-ketone iron chelating agent as shown in a formula (III) which is described in the specification. The synthetic method comprises the following steps: with methyl-protected azido hydroxypyridone as shown in a formula (I) which is described in the specification as a raw material, allowing the methyl-protected azido-hydroxypyridine to generate reduction and demethylation reactions under the protection of boron tribromide as shown in a formula (II) which is described in the specification, a solvent A and gas B, after completion of the reactions, carrying out quenching with a solvent C, and carrying out post-treatment so as to obtain the amino-containing 3-hydroxypyridine-4-ketone compound as shown in the formula (III). Compared with a conventional method, the synthetic method provided by the invention adopts a boron tribromide reagent with mild reaction conditions, avoids the use of a metal catalyst, andhas simple and convenient operation and high reaction yield.

Synthesis, antiplasmodial activity, and β-hematin inhibition of hydroxypyridone-chloroquine hybrids

A series of noncytotoxic 4-aminoquinoline-3-hydroxypyridin-4-one hybrids were synthesized on the basis of a synergistic in vitro combination of a precursor N-alkyl-3-hydroxypyridin-4-one with chloroquine (CQ) and tested in vitro against CQ resistant (K1 and W2) and sensitive (3D7) strains of Plasmodium falciparum. In vitro antiplasmodial activity of the precursors was negated by blocking the chelator moiety via complexation with gallium(III) or benzyl protection. None of the precursors inhibited β-hematin formation. Most hybrids were more potent inhibitors of β-hematin formation than CQ, and a correlation between antiplasmodial activity and inhibition of β-hematin formation was observed. Potent hybrids against K1, 3D7, and W2, respectively, were 8c (0.13, 0.004, and 0.1 μM); 8d (0.08, 0.01, and 0.02 μM); and 7g (0.07, 0.03, and 0.08 μM).