61049-67-0

Usage

Uses

Used in Pharmaceutical Industry:
3-(Benzyloxy)-4H-pyran-4-one is used as a key intermediate in the synthesis of various pharmaceutical products due to its beneficial medicinal properties. These properties include antioxidant, anti-microbial, anti-inflammatory, and anti-cancer traits, making it a valuable compound for the development of new drugs and treatments.
Used in Synthesis of Antioxidants:
3-(Benzyloxy)-4H-pyran-4-one is used as a precursor in the synthesis of antioxidant compounds, which are essential in preventing oxidative damage in biological systems and have potential applications in the prevention and treatment of various diseases.
Used in Synthesis of Anti-microbial Agents:
3-(benzyloxy)-4H-pyran-4-one is utilized as a starting material in the production of anti-microbial agents, which are crucial in combating infections and maintaining public health.
Used in Synthesis of Anti-inflammatory Drugs:
3-(Benzyloxy)-4H-pyran-4-one is employed as a building block in the creation of anti-inflammatory drugs, which are used to reduce inflammation and alleviate pain in various medical conditions.
Used in Synthesis of Anti-cancer Agents:
3-(Benzyloxy)-4H-pyran-4-one is used as a component in the development of anti-cancer agents, which are designed to target and eliminate cancer cells while minimizing damage to healthy cells.

InChI:InChI=1/C12H10O3/c13-11-6-7-14-12(8-11)15-9-10-4-2-1-3-5-10/h1-8H,9H2

Upstream product

• 1219-33-6 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid 
• 496-63-9 3-hydroxy-pyran-4-one 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 15771-06-9 5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 

Downstream Products

• 362598-68-3 3-benzyloxy-1-(2-piperidin-1-yl-ethyl)-1H-pyridin-4-one 
• 362598-71-8 3-benzyloxy-1-(2-morpholin-4-yl-ethyl)-1H-pyridin-4-one 
• 362598-69-4 3-benzyloxy-1-(2-pyridin-2-yl-ethyl)-1H-pyridin-4-one 
• 362598-70-7 3-benzyloxy-1-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-1H-pyridin-4-one 
• 959327-48-1 3-benzyloxy-1-thiazolinomethyl-4(1H)-pyridone 
• 959676-13-2 3-benzyloxy-1-thiazolinoethyl-4(1H)-pyridone 
• 496-63-9 3-hydroxy-pyran-4-one 
• 1333331-84-2 3-[(4-methoxybenzyl)oxy]-4H-pyran-4-one 
• 1333331-85-3 3-[(4-methoxybenzyl)oxy]pyridin-4(1H)-one 
• 1333331-86-4 4'-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one 
• 1333331-87-5 {3-[(4-methoxybenzyl)oxy]-4-oxo-4H-1,2'-bipyridin-4-yl}boronic acid 
• 1333331-88-6 3-[(4-methoxybenzyl)oxy]-4'-phenyl-[1,2']bipyridinyl-4-one 
• 1333331-89-7 6'-bromo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one 
• 1333331-90-0 3'-fluoro-4'-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one 

Relevant academic research and scientific papers

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 hybrid pyridinone amide derivative with potential anti-AD activity and preparation method and application of derivative

The invention discloses a coumarin hybrid pyridinone amide derivative and a preparation method and application thereof. The coumarin hybrid pyridinone amide derivative and pharmacologically acceptablesalt thereof are shown in the formula (I) and the formula (II), and the derivative can be used for preparing drugs for resisting the Alzheimer's disease, the Parkinson's disease or treating other diseases or symptoms by suppressing monoamine oxidase, chelating metallic iron ions, resisting A and resisting oxidation.

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.

INHIBITORS OF CATECHOL O-METHYL TRANSFERASE AND THEIR USE IN THE TREATMENT OF PSYCHOTIC DISORDERS

The present invention relates to 4-pyridinone compounds which are inhibitors of catechol O-methyltransferase (COMT), and are useful in the treatment and prevention of neurological and psychiatric disorders and diseases in which COMT enzyme is involved. The present invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which COMT is involved

Pyrones to pyrans: Enantioselective radical additions to acyloxy pyrones

This paper describes a highly site-, diastereo-, and enantioselective intermolecular radical addition/hydrogen atom transfer to hydroxypyrone pyromeconic and kojic acids. The methodology can be extended to the formation of chiral quaternary centers. The p

Design, synthesis, and evaluation of novel 2-substituted 3-hydroxypyridin-4-ones: Structure-activity investigation of metalloenzyme inhibition by iron chelators

A range of novel 3-hydroxypyridin-4-ones with different R2 substitutents has been synthesized for the investigation of the structure-activity relationship between the chemical nature of the ligand and the inhibitory activity of the iron-contain

Synthesis of 4(1H)-pyridinone derivatives and investigation of analgesic and antiinflammatory activities

This paper describes recent result of a research program aimed at the synthesis and pharmacological evaluation of new 4(1H)-pyridinone derivatives belonging to the 1,3-disubstituted series (4-11). These compounds were structurally planned by applying the molecular hybridization strategy on previously described 1,2-disubstituted-4(1H)-pyridinone derivatives, considered as lead compounds, which present potent analgesic properties (M. D. Aytemir, T. Uzbay, D. D. Erol, Arzneim. Forsch. (Drug Res.) 49 (1999) 250). Their chemical structures have been proved by means of their IR and 1H NMR data and by elemental analysis. The analgesic profile of the title compounds (4-11), evaluated by the model of abdominal constrictions induced by acetic acid, showed that all the 4(1H)-pyridinone derivatives were active, exhibiting an analgesic activity comparable with that of aspirin (acetyl salicylic acid) used as a standard. The antiinflammatory profile by the synthesized compounds, evaluated by the model of carrageenan rat paw edema, showed that all compounds were active and were comparable with indomethacin used as a standard.

Synthesis, physicochemical properties, and biological evaluation of hydroxypyranones and hydroxypyridinones: Novel bidentate ligands for cell- labeling

The synthesis of a range of hydroxypyranones and hydroxypyridinones with potential for the chelation of indium(III) is described. The crystal structures of two of the indium complexes are presented. The distribution coefficients of the ligands and the corresponding iron(III), gallium(III), and indium(III) complexes are reported. Good linear relationships between the distribution coefficients of the iron and gallium complexes and iron and indium complexes were obtained. In contrast a nonlinear relationship was obtained between the distribution coefficient of the free ligand and the distribution coefficient of the three groups of complexes. This latter relationship was used to identify compounds with optimal cell labeling properties. Two such compounds both 6-(alkoxymethyl)-3-hydroxy-4H-pyran-4- ones have been compared with tropolone for their ability to label human leucocytes with 111In. The leucocyte labeling efficiencies of the selected ligands were greater and the in-vitro plasma stabilities were similar to that of 111In-tropolonate. These results suggest that the new bidentate ligands may offer advantages over those currently used for cell-labeling.

Synthesis and antimicrobial investigation of thiazolinoalkyl-4(1H)-pyridones

A number of thiazolinoalkyl-4(1H)-pyridones have been synthesized using 4-pyrone derivatives with cysteamine HCI, and their antibacterial and antifungal activities have been tested. Their chemical structures have been proved by means of their IR, 1H-NMR, mass spectroscopic data and by elemental analysis. Investigation of antimicrobial activity of compounds was done by tube dilution and disk tecniques using bacteria (Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Streptococcus faecalis RSKK 10541) and yeast-like fungi (Candida parapsilosis, C albicans, C pseudotropicalis, C stellatoidea). A significant inhibitory effect was recorded for many compounds against C albicans (7a, c, d; minimal inhibitory concentration (MIC) = 12.5-25 μg/ml), S aureus ATCC 25923 (4c, 7a; MIC = 25 μg/ml), P aeruginosa ATCC 27923 (7a; MIC = 75 μg/ml), S faecalis RSKK 10541 (4c; MIC = 25 μg/ml), C pseudotropicalis (46, 6d, 7c; MIC = 25 μg/ml) and C stellatoidea (4d; MIC = 25 μg/ml).