15771-06-9

Usage

Uses

Used in Pharmaceutical Industry:
5-(Benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one is used as a reagent for the synthesis of hydroxypyridinone-L-phenylalanine conjugates. These conjugates are considered potential tyrosinase inhibitors, which can be beneficial in the development of treatments for conditions related to excessive melanin production, such as hyperpigmentation or melasma.
Used in Cosmetic Industry:
As a derivative of Kojic Acid, 5-(Benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one may also find applications in the cosmetic industry, where tyrosinase inhibitors are often used to create skin-lightening or brightening products. The compound's ability to inhibit tyrosinase, an enzyme responsible for melanin production, makes it a valuable ingredient in formulations aimed at reducing the appearance of dark spots and uneven skin tone.

Upstream product

• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 100-44-7 benzyl chloride 
• 89539-54-8 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 
• 100-39-0 benzyl bromide 
• 7732-18-5 water 

Downstream Products

• 89539-51-5 5-(benzyloxy)-2-(hydroxymethyl)-1-methyl-1,4-dihydropyridin-4-one 
• 181431-42-5 5-Benzyloxy-2-ethoxymethyl-pyran-4-one 
• 89539-54-8 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 
• 812653-96-6 2-phthalimidomethyl-5-benzyloxypyran-4-one 
• 1219-33-6 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid 
• 107758-06-5 methyl 5-benzyloxy-4-oxo-4H-pyran-2-carboxylate 
• 40838-34-4 2-chloromethyl-5-methoxy-4H-pyran-4-one 
• 1381864-87-4 (E)-5-(benzyloxy)-2-(3,4-dimethoxystyryl)-4H-pyran-4-one 
• 1334399-73-3 (E)-2-(3,4-dihydroxystyryl)-5-hydroxy-4H-pyran-4-one 
• 1381864-92-1 5-(benzyloxy)-2-((3-hydroxyphenoxy)methyl)-4H-pyran-4-one 
• 1381864-94-3 5-hydroxy-2-((3-hydroxyphenoxy)methyl)-4H-pyran-4-one 
• 1381864-95-4 5-(benzyloxy)-2-((4-(phenylsulfonyl)piperazin-1-yl)methyl)-4H-pyran-4-one 
• 1381864-96-5 5-hydroxy-2-((4-(phenylsulfonyl)piperazin-1-yl)methyl)-4H-pyran-4-one 
• 1381864-85-2 diethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate 

Relevant academic research and scientific papers

Synthesis, anti-HIV-1 and antiproliferative evaluation of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety

In an effort to synthesize more effective non-nucleoside reverse transcriptase inhibitors (NNRTIs) against the HIV-1 infection, a new series of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety were designed by molecular docking studies, prepared and characterized by spectroscopic techniques. All the synthesized compounds were in vitro evaluated for their inhibitory effect against the HIV-1 replication in the MT-4 cells. Results showed that none of these synthesized compounds displayed any specific anti HIV-1 activity. Surprisingly, these compounds showed high cytotoxicity against MT-4 cells with low selectivity index (50 = 1.3 μM and EC50 = 1.8 μM respectively).

Design, synthesis and anti-HIV-1 evaluation of a series of 5-hydroxypyridine-4-one derivatives as possible integrase inhibitors

A series of 5-hydroxypyridine-4-one derivatives were synthesized and subjected to HIV-1 replication inhibition assay. Docking studies provide a detailed molecular binding model for this class of compounds interacting with integrase enzyme. All of the deri

Molecular dynamics simulation and 3D-pharmacophore analysis of new quinoline-based analogues with dual potential against EGFR and VEGFR-2

Epidermal growth factor and vascular endothelial growth factor-2 are important targets of tyrosine kinase for the treatment of various cancerous diseases. Combination of inhibition of both targets to produce synergy in the signal pathway is a critical approach to identify novel tyrosine kinase inhibitors. In this study, a series of new compounds derived from the 4-aminoquinoline as dual inhibitors were synthesized. The obtained results of cytotoxicity assay against human carcinoma cell lines indicated 0.8 μM for 4c against A549 showing its high efficiency in comparison to erlotinib. Pharmacophore modeling as a structure-based method was investigated on dual inhibitors and 4c which was compared with co-crystallized in the active site of EGFR and VEGFR-2. They have shown the same binding orientation as vandetanib, erlotinib and sorafenib. Molecular dynamics simulation results approved that Met769, Lys721, Asp1046, and Lys868 are key residues in two binding sites for dual activity. Ala1050 and Pro968 were identified as new amino acid interaction sites for dual inhibition. 4c showed more favorable stability than vandetanib in VEGFR-2 receptor for a 50 ns dynamic simulation. The high correlation between essential pharmacophoric features of designed compounds and lead inhibitors interactions provided a deeper insight into the structural basis of 4-aminoquinoline inhibition.

Synthesis of new kojic acid based unnatural α-amino acid derivatives

An efficient method for the preparation of kojic acid based α-amino acid derivatives by alkylation of glycinate schiff base with bromokojic acids have been described. Using this method, mono as well as di alkylated kojic acid-amino acid conjugates have been prepared. This is the first synthesis of C-linked kojic acid-amino acid conjugate where kojic acid is directly linked to amino acid through a C-C bond.

Synthesis and biological evaluation of deferiprone-resveratrol hybrids as antioxidants, Aβ1–42aggregation inhibitors and metal-chelating agents for Alzheimer's disease

A series of deferiprone-resveratrol hybrids have been designed and synthesized as multitarget-directed ligands (MTDLs) through merging the chelating moiety 3-hydroxypyridin-4-one into the structure of resveratrol, a natural antioxidant agent and β-amyloid peptide (Aβ) aggregation inhibitor. The in?vitro biological evaluation revealed that most of these newly synthesized compounds exhibited good inhibitory activity against self-induced Aβ1–42aggregation, excellent antioxidant activity and potent metal chelating capability. Compounds 3i and 4f were identified as the most promising MTDLs with triple functions, possessing micromolar IC50values for Aβ1–42aggregation inhibition, greater 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS?+) scavenging activity than Trolox and similar pFe(III) values to that of deferiprone.

Hydroxypyridinones with enhanced iron chelating properties. Synthesis, characterization and in vivo tests of 5-hydroxy-2-(hydroxymethyl)pyridine- 4(1H)-one

The synthesis of 5-hydroxy-2-(hydroxymethyl)pyridin-4(1H)-one (P1) is presented, together with the evaluation of its coordination ability towards Fe3+, studied by a combination of chemical, computational, and animal approaches. The use of complementary analytical techniques has allowed us to give evidence of the tautomeric changes of P1 as a function of pH, and to determine their influence on the coordinating ability of P1 towards Fe3+. The pFe3+ value 22.0 of P1-iron complexes is noticeably higher than that of deferiprone (20.6), one of the three clinical chelating agents in therapeutic use for iron overload diseases. This is due on one side to the tautomeric change to the catechol form, and on the other to the lower protonation constant of the OH group. Bio-distribution studies on mice allowed us to confirm in vivo the efficacy of P1. Furthermore the coordinating ability toward Al3+, Cu2+ and Zn2+ has been studied to evaluate the possible use of P1 against a second toxic metal ion (Al3+), and to envisage its potential influence on the homeostatic equilibria of essential metal ions. The chelating ability of P1 toward these ions, not higher than that of the corresponding deferiprone, contributes to render P1 a more selective iron chelator.

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.

Pyridone hexa-alkyne amine modified derivative and preparation method and application thereof

The invention relates to a pyridone hexa-alkyne amine modified derivative as shown in a formula (I) and a pharmaceutically acceptable salt thereof, a preparation method thereof, application of the pyridone hexa-alkyne amine modified derivative or the pharmaceutically acceptable salt thereof to preparation of drugs for preventing or treating related diseases, especially Alzheimer's disease and Parkinson's disease, by inhibiting monoamine oxidase, chelating metal iron ions, resisting Abeta and resisting oxidation. According to the invention, a series of novel single-molecule multi-target anti-ADactive compounds are synthesized, and pyridone derivatives with iron ion chelating activity and propynylamine with MAOB inhibitory activity are creatively and organically combined together, so that the compounds have remarkable advantages on Alzheimer's disease with complex pathogenesis; and the combined molecules are far superior to CP20 (deferiprone) in the aspect of iron ion chelating activity.

ALA hybrid 3-hydroxypyridone derivative as well as preparation method and application thereof

The invention designs and synthesizes a novel anti-tumor active compound with iron chelating property and photosensitive activity based on the principles of reasonable drug design, drug-likeness and the like. The invention aims to provide a preparation me

N-Propargylamine-hydroxypyridinone hybrids as multitarget agents for the treatment of Alzheimer's disease

AD is a progressive brain disorder. Because of the lack of remarkable single-target drugs against neurodegenerative disorders, the multitarget-directed ligand strategy has received attention as a promising therapeutic approach. Herein, we rationally designed twenty-nine hybrids of N-propargylamine-hydroxypyridinone. The designed hybrids possessed excellent iron-chelating activity (pFe3+ = 17.09–22.02) and potent monoamine oxidase B inhibitory effects. Various biological evaluations of the optimal compound 6b were performed step by step, including inhibition screening of monoamine oxidase (hMAO-B IC50 = 0.083 ± 0.001 μM, hMAO-A IC50 = 6.11 ± 0.08 μM; SI = 73.5), prediction of blood–brain barrier permeability and mouse behavioral research. All of these favorable results proved that the N-propargylamine-hydroxypyridinone scaffold is a promising structure for the discovery of multitargeted ligands for AD therapy.