4780-14-7

Basic information

• Product Name: 3-Methoxy-2-Methyl-pyran-4-one
• Synonyms: 3-Methoxy-2-Methyl-pyran-4-one;3-Methoxy-2-Methyl-4H-pyran-4-one;2-Methyl-3-methoxy-4H-pyran-4-one;3-methoxy-2-methyl-4-pyranone;InChI=1/C7H8O3/c1-5-7(9-2)6(8)3-4-10-5/h3-4H,1-2H;MFCD14553191
• CAS NO: 4780-14-7
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.13662
• EINECS: -0
• Mol File: 4780-14-7.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 279.6°C at 760 mmHg
• Flash Point: 113.6°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0.00397mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-Methoxy-2-Methyl-pyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxy-2-Methyl-pyran-4-one(4780-14-7)
• EPA Substance Registry System: 3-Methoxy-2-Methyl-pyran-4-one(4780-14-7)

Safety Data

• Hazardous Substances Data: 4780-14-7(Hazardous Substances Data)

Usage

Uses

3-Methoxy-2-methyl-4H-pyran-4-one is a reagent used in the synthesis of Staphylococcus antibacterials.

InChI:InChI=1/C7H8O3/c1-5-7(9-2)6(8)3-4-10-5/h3-4H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 118-71-8 Maltol 
• 61049-69-2 3-O-benzylmaltol 
• 77-78-1 dimethyl sulfate 
• 75-52-5 nitromethane 
• 82209-15-2 C₈H₁₁O₃⁽¹⁺⁾*FO₃S^(1-) 
• 6814-64-8 methylenedimethyl sulfurane 
• 74-88-4 methyl iodide 

Downstream Products

• 54312-21-9 N-(p-tolyl)-3-methoxy-2-methyl-4-pyridone 
• 127394-38-1 3-Methoxy-1-(4-methoxy-phenyl)-2-methyl-1H-pyridin-4-one 
• 127394-39-2 N-(4-nitrophenyl)-3-methoxy-2-methyl-4-pyridone 
• 54312-20-8 3-Methoxy-2-methyl-1-phenyl-1H-pyridin-4-one 
• 76015-11-7 3-methoxy-2-methylpyridin-4(1H)-one 
• 1436415-54-1 methyl 2-{6-[1-((tert-butyldimethylsilyl)oxy)propyl]-5-methoxy-4-oxo-4H-pyran-3-carbonyl}-3,5-dimethoxybenzoate 
• 127394-43-8 3-Hydroxymethyl-2-methyl-1-(4-nitro-phenyl)-1H-pyridin-4-one 
• 127394-42-7 3-Hydroxymethyl-1-(4-methoxy-phenyl)-2-methyl-1H-pyridin-4-one 
• 127394-41-6 N-(p-tolyl)-3-hydroxymethyl-2-methyl-4-pyridone 
• 76349-10-5 2-methyl-3-<<(methylamino)carbonyl>oxy>-4(1H)-pyridone 
• 17184-20-2 2-methyl-3-acetoxy-4(1H)-pyridone 
• 17184-19-9 3-hydroxy-2-methylpyrid-4-one 
• 107512-35-6 3,4-dimethoxy-2-methylpyridine 

Relevant articles and documents

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Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity

A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe3+ values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-β1-42 (Aβ1-42) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.

Coumarin heterozygous pyridone compounds having iron chelation and monoamine oxidase B inhibitory activity as well as preparation and application of compounds

The invention discloses coumarin/pyridone heterozygous derivatives represented by a formula (I) shown in the description or a pharmaceutically-acceptable salt of the derivatives. The preparation method of the coumarin/pyridone heterozygous derivatives comprises the following steps: one pyridone derivative represented by a formula 3 shown in the description is obtained by a series of synthesis by using one hydroxypyrone with different substituent groups represented by a formula 1 shown in the description as a raw material; and a compound represented by a formula 4 shown in the description is subjected to a condensation reaction to obtain a compound represented by a formula 5 shown in the description, one-step bromination is performed to obtain a compound represented by a formula 6 shown inthe description, the compound represented by the formula 6 and the pyridone derivative represented by the formula 3 are subjected to a one-step nucleophilic substitution reaction to obtain a compoundrepresented by a formula 7 shown in the description, and finally an alkyl protecting group in a pyridone structure is removed to obtain one target compound represented by the formula (I). The compounds provided by the invention are a novel series of single-molecular multi-target series drugs, and have iron chelation, targeted MAO-B inhibitory activity, antioxidant activity, unique advantages for an Alzheimer disease with complicated pathogenesis, a clear mechanism of action and excellent 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.