18234-41-8

Usage

Structure

Pyran ring with a carboxaldehyde functional group (at position 2) and a phenylmethoxy group (at position 5)

Functional Groups

Carboxaldehyde (-CHO) group
Phenylmethoxy group (phenyl group attached to a methoxy group)

Usage

Organic synthesis
Medicinal chemistry
Production of pharmaceuticals and agrochemicals

Applications

Building block in pharmaceutical synthesis
Building block in agrochemical synthesis
Flavoring agent in the food industry

Versatility

Intermediate in the synthesis of various organic compounds
Potential biological activities due to its unique structure

Aromatic Properties

Suitable for flavoring due to aromatic characteristics

Upstream product

• 89539-54-8 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 
• 15771-06-9 5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one 
• 100-44-7 benzyl chloride 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 100-39-0 benzyl bromide 

Downstream Products

• 1064077-41-3 5-benzyloxy-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-pyran-4-one 
• 1064076-87-4 5-benzyloxy-2-difluoromethyl-pyran-4-one 
• 1449029-96-2 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(tert-butylcarbamoyl)methyl]-2-chloro-N-(4-methoxyphenyl)benzamide 
• 1449029-93-9 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(tert-butylcarbamoyl)methyl]-2-chloro-N-p-tolylbenzamide 
• 1449029-95-1 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(tert-butylcarbamoyl)methyl]-N-(4-butyl-phenyl)-2-chlorobenzamide 
• 1449029-91-7 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(tert-butylcarbamoyl)methyl]-N-phenylbenzamide 
• 1449029-97-3 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(cyclohexylcarbamoyl)methyl]-2-chloro-N-(4-chlorophenyl)benzamide 
• 1449029-90-6 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(cyclohexylcarbamoyl)methyl]-2-chloro-N-phenylbenzamide 
• 1449029-92-8 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(cyclohexylcarbamoyl)methyl]-2-chloro-N-p-tolylbenzamide 
• 1449029-98-4 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(cyclohexylcarbamoyl)methyl]-N-(4-chlorophenyl)benzamide 
• 1449029-94-0 N-[(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)(cyclohexylcarbamoyl)methyl]-N-p-tolylbenzamide 

Relevant academic research and scientific papers

Synthesis of novel isoxazole derivatives bearing kojic acid moiety and evaluation of their antimicrobial activity

[Figure not available: see fulltext.] A novel series of 3,5-disubstituted isoxazoles bearing kojic acid moiety were synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of terminal alkynes with nitrile oxide formed in situ from the corresponding hydroximoyl chloride. Structures of the synthesized compounds were characterized using spectroscopic analysis data. Antimicrobial activity of the isoxazole conjugates was determined as MIC values by broth microdilution method against different bacteria: Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Salmonella typhi, and fungi Candida kefyr. The obtained results revealed notable antibacterial and antifungal activities of the compounds.

Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity

In an attempt to synthesise new tyrosinase inhibitors, we designed and synthesised a series of chalcone-hydroxypyridinone hybrids as potential tyrosinase inhibitors adopting strategic modifications of kojic acid. All the newly synthesised compounds were characterised by NMR and mass spectrometry. Initial screening of the target compounds demonstrated that compounds 1a, 1d, and 1n had relatively strong inhibitory activities against tyrosinase monophenolase, with IC50 values of 3.07 ± 0.85, 2.25 ± 0.8 and 2.75 ± 1.19 μM, respectively. The inhibitory activity against monophenolase was 6- to 8-fold higher than that of kojic acid. Compounds 1a, 1d, and 1n also showed inhibition of diphenolase, with IC50 values of 17.05 ± 0.07, 11.70 ± 0.03 and 19.3 ± 0.28 μM, respectively. The inhibition kinetics of diphenolase indicates that compounds 1a and 1d induce reversible inhibition on tyrosinase. Finally, we found that copper coordination should be one of the important inhibitory mechanism of these compounds in tyrosinase.

Hydroxypyridinone derivative of aza-chalcone structure, preparation method and application

The invention discloses a hydroxypyridinone derivative of an aza-chalcone structure. According to a structural formula I, X is O and N-CnH2N+1(n=0-12); R2 is H, 4-F, 2-OH, 4-OCH3, 3,4-di-OCH3 and 3,4-di-OH. The invention further discloses a preparation me

COMT INHIBITING METHODS AND COMPOSITIONS

Compounds that inhibit COMT enzyme and pharmaceutical compositions comprising the same are provided herein. Methods of treating various psychiatric and neurological disorders with the compounds and pharmaceutical compositions described herein are also provided.

Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media

An efficient green method for the syntheses of biologically active xanthene derivatives by use of zeolite-supported transition metal catalysts is described. A Fe-Cu/ZSM-5 heterogeneous catalyst has the highest activity in the one-pot syntheses with a wide

Oxidative aza Michael addition of nitrogen-containing heterocycles to kojic acid-derived Baylis-Hillman adducts

The oxidation of Baylis-Hillman adducts, obtained by the reaction of 5-benzyloxy-2-formyl-4-pyrone, with o-iodoxybenzoic acid generates β-ketomethylene intermediates that in situ undergo conjugative attack of NH-containing heterocycles such as imidazole a

The modified runflat carbocation kojic/cyclodextrin and its complex manufacturing method

PROBLEM TO BE SOLVED: To provide a carborane-modified kojic acid/cyclodextrin inclusion complex having excellent solubility with water.SOLUTION: A complex of a cyclodextrin derivative and a carborane-modified kojic acid is prepared. The preparation process includes a step of vibrating a mixture of the cyclodextrin derivative and the carborane-modified kojic acid.

Synthesis, spectroscopic and DFT studies of novel fluorescent dyes: 3-Aminoimidazo[1,2-a]pyridines possessing 4-pyrone moieties

A series of novel imidazo[1,2-a]pyridines possessing 4-pyrone ring were synthesized by three-component condensation of 4-pyrone carbaldehydes, 2-aminopyridines and isocyanides. Bismuth (III) chloride was used as a catalyst in these reactions and desired products were synthesized in good yields at a very short period of time under solvent free conditions. UV-Vis absorption and fluorescence emission spectra of these compounds were investigated. It shown that two of these compounds (10f and 10g) exhibit intense fluorescence in dichloromethane. Optimized ground-state molecular geometries and orbital distributions of these two fluorescent dyes were obtained using density functional theory (DFT). Thermogravimetric analysis and electrochemical properties of these compounds were also studied.

Cytotoxic activity assessment, QSAR and docking study of novel bis-carboxamide derivatives of 4-pyrones synthesized by Ugi four-component reaction

Fourteen novel bis-carboxamide derivatives of 4-pyrones were designed and synthesized via Ugi four-component reactions of 4-pyrone carbaldehydes, aromatic amines, isocyanides and carboxylic acids. The cytotoxic activity of synthesized derivatives was eval

Synthesis of fused pyrimidone derivatives of 4-pyrones from the acetates of Baylis-Hillman adducts

A series of fused pyrimidone derivatives of 4-pyrones was synthesized by conversion of the acetates of Baylis-Hillman adducts obtained from 2-formyl-4-pyrones with 2-aminopyridine and 2-aminothiazole.