1199-60-6

Basic information

• Product Name: 4H-Pyran-2-carboxylic acid, 5-methoxy-4-oxo-
• Synonyms: 4H-Pyran-2-carboxylic acid, 5-methoxy-4-oxo-
• CAS NO: 1199-60-6
• Molecular Formula: C₇H₆O₅
• Molecular Weight: 170.12
• Mol File: 1199-60-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 282 °C
• Boiling Point: 398.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• PKA: 1.70±0.20(Predicted)
• CAS DataBase Reference: 4H-Pyran-2-carboxylic acid, 5-methoxy-4-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyran-2-carboxylic acid, 5-methoxy-4-oxo-(1199-60-6)
• EPA Substance Registry System: 4H-Pyran-2-carboxylic acid, 5-methoxy-4-oxo-(1199-60-6)

Safety Data

• Hazardous Substances Data: 1199-60-6(Hazardous Substances Data)

Usage

Chemical compound

4H-Pyran-2-carboxylic acid, 5-methoxy-4-oxo-

Upstream product

• 6269-25-6 2-Hydroxymethyl-5-methoxy-4H-pyran-4-on 
• 499-78-5 comenic acid 
• 77-78-1 dimethyl sulfate 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 35438-43-8 5-methoxy-4H-pyran-4-one-2-carboxaldehyde 
• 74-88-4 methyl iodide 

Downstream Products

• 1394231-88-9 N-(2-(tert-butyldiphenylsiloxy)ethyl)-6-(2-(6-chloroquinolin-2-yl)thiazol-4-yl)-5-methoxy-1-methyl-3-(methylthio)-4-oxo-1,4-dihydropyridine-2-carboxamide 
• 1394231-79-8 (2-(tert-butyldiphenylsilyloxy)ethyl)-5-methoxy-N-methyl-4-oxo-1,4-dihydropyridine-2-carboxamide 
• 1394231-80-1 (2-(tert-butyldiphenylsilyloxy)ethyl)-5-methoxy-N,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide 
• 1394231-81-2 (2-(tert-butyldiphenylsilyloxy)ethyl)-6-iodo-5-methoxy-N-methyl-4-oxo-1,4-dihydropyridine-2-carboxamide 
• 1394231-82-3 3-bromo-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methoxy-N-methyl-4-oxo-1,4-dihydropyridine-2-carboxamide 
• 1394231-83-4 (2-(tert-butyldiphenylsilyloxy)ethyl)-5-methoxy-N-methyl-3-(methylthio)-4-oxo-1,4-dihydropyridine-2-carboxamide 
• 1394231-84-5 (2-(tert-butyldiphenylsilyloxy)ethyl)-6-iodo-5-methoxy-N-methyl-3-(methylthio)-4-oxo-1,4-dihydropyridine-2-carboxamide 
• 1394231-78-7 (2-(tert-butyldiphenylsilyloxy)ethyl)-5-methoxy-4-oxo-4H-pyran-2-carboxamide 
• 1193-64-2 3-methoxy-4H-pyran-4-one 
• 50700-60-2 3-methoxy-4(1H)-pyridone 
• 857433-67-1 methyl 4-chloro-5-methoxypyridine-2-carboxylate 
• 5878-19-3 Methoxyacetone 
• 144-62-7 oxalic acid 
• 353460-76-1 5-methoxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid 

Relevant articles and documents

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.

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.

Systematic comparison of the mono-, dimethyl-and trimethyl 3-hydroxy-4(1H)-pyridones-Attempted optimization of the orally active iron chelator, deferiprone

A range of close analogues of deferiprone have been synthesised. The group includes mono-, di-and trimethyl-3-hydroxy-4(1H)-pyridones. These compounds were found to possess similar pFe3+ values to that of deferiprone, with the exception of the 2.5-dimethylated derivatives. Surprisingly the NHcontaining hydroxy-4(1H)-pyridones were found to be marginally more lipophilic than the corresponding N-Me containing analogues. This same group are also metabolised less efficiently by Phase 1 hydroxylating enzymes than the corresponding N-Me analogues. As result of this study, three compounds have been identified for further investigation centred on neutropenia and agranulocytosis.