59281-14-0

Usage

Uses

Used in Pharmaceutical Research:
5-(benzyloxy)-2-(hydroxymethyl)pyridin-4-ol is used as a research compound for studying the P2X7 receptor's role in inflammation, pain, and neurodegenerative diseases. Its agonistic properties allow researchers to investigate the receptor's function and potential therapeutic applications.
Used in Drug Development:
In the pharmaceutical industry, 5-(benzyloxy)-2-(hydroxymethyl)pyridin-4-ol is used as a potential therapeutic target for the development of treatments for chronic pain, rheumatoid arthritis, and multiple sclerosis. Its ability to modulate the P2X7 receptor makes it a promising candidate for the development of new drugs targeting these conditions.
Used in Immunology Research:
5-(benzyloxy)-2-(hydroxymethyl)pyridin-4-ol is used as a tool in immunology research to understand the role of purinergic signaling in immune cell function and inflammatory responses. Its ability to induce cytokine release through the P2X7 receptor helps researchers explore the complex interactions between immune cells and their environment.
Used in Neuroscience Research:
In the field of neuroscience, 5-(benzyloxy)-2-(hydroxymethyl)pyridin-4-ol is used to study the involvement of the P2X7 receptor in neurodegenerative diseases. Its agonistic effects on the receptor provide insights into the potential role of purinergic signaling in the progression of these diseases and the development of therapeutic strategies.
Used in Toxicology Studies:
5-(benzyloxy)-2-(hydroxymethyl)pyridin-4-ol is used in toxicology studies to evaluate the safety and potential side effects of compounds targeting the P2X7 receptor. Its ability to induce inflammatory responses and cytokine release can help researchers assess the risks associated with the development of new drugs and therapies.

Upstream product

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

Downstream Products

• 443955-89-3 (2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)-methanol 
• 736088-02-1 6-hydroxymethyl-3,4-pyridinediol 
• 31883-16-6 6-hydroxymethyl-3-hydroxy-4-pyridinone 
• 166742-48-9 5-(benzyloxy)-2-((trityloxy)methyl)pyridin-4(1H)-one 
• 112334-68-6 1,4-dihydro-4-oxo-2-[(hydroxy)(methoxy)methyl]-5-(phenylmethoxy)pyridine 
• 113603-41-1 2-((1-Hydroxy-1-methoxy)methyl)-5-(phenylmethoxy)-4(1H)-pyridinone 
• 959616-78-5 (5-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl acetate 
• 1338821-40-1 [5-(benzyloxy)-4-isopropoxypyridin-2-yl]methanol 
• 1259499-09-6 5-(benzyloxy)-3-chloro-2-(hydroxymethyl)pyridin-4(1H)-one 
• 1338729-33-1 C₁₃H₁₀ClNO₃ 
• 1338729-34-2 5-(benzyloxy)-3-chloro-4-oxo-1,4-dihydropyridine-2-carboxylic acid 
• 1338729-35-3 C₁₉H₂₂ClN₃O₃ 
• 1338821-42-3 5-(benzyloxy)-2-(bromomethyl)-4-isopropoxypyridine 
• 1338821-45-6 (5R,7S)-8-{[5-(benzyloxy)-4-isopropoxypyridin-2-yl]methyl}-1-(3-fluorophenyl)-7-methyl-2-thia-1,8-diazaspiro[4.5]dec-3-ene 2,2-dioxide 

Relevant academic research and scientific papers

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.

Development of the Convergent, Kilogram-Scale Synthesis of an Antibacterial Clinical Candidate Using Enantioselective Hydrogenation

Early chemical development studies into the best way of assembling AZD9742, an antibacterial drug candidate, have involved swapping the order of two reductive aminations. The orthogonally functionalized aminopiperidine partner for these couplings is now enantioselectively synthesized using ruthenium-catalyzed asymmetric hydrogenation. The challenge of controlling defluorination through an appropriate catalyst choice has hitherto prevented this revised sequence from reaching its full potential. However, it is still shown to allow access to the active pharmaceutical ingredient in a stereochemically pure form and has been demonstrated on a multikilogram scale. The reductive aminations in both the original and revised sequences provided different scale-up challenges, and the solutions implemented are described.

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

Novel compounds that are inhibitors of YAP/TAZ-TEAD interaction and their use in the treatment of malignant mesothelioma

These compounds are useful as inhibitors of the YAP/TAZ-TEAD interaction.

Discovery of Novel Pyridone-Conjugated Monosulfactams as Potent and Broad-Spectrum Antibiotics for Multidrug-Resistant Gram-Negative Infections

Conjugating a siderophore to an antibiotic is a promising strategy to overcome the permeability-mediated resistance of Gram-negative pathogens. On the basis of the structure of BAL30072, novel pyridone-conjugated monosulfactams incorporating diverse substituents into the methylene linker between the 1,3-dihydroxypyridin-4(1H)-one and the aminothiazole oxime were designed and synthesized. Structure-activity relationship studies revealed that a variety of substituents were tolerated, with isopropyl (compound 12c) and methylthiomethyl (compound 16a) showing the best efficacy against multidrug-resistant (MDR) Gram-negative pathogens. In addition, compound 12c exhibits a good free fraction rate in an in vitro human plasma protein binding test, along with a low clearance and favorable plasma exposure in vivo. In a murine systemic infection model with MDR Klebsiella pneumoniae, compound 12c shows an ED50 of 10.20 mg/kg. Taken together, the results indicate that compound 12c is a promising drug candidate for the treatment of serious infections caused by MDR Gram-negative pathogens.

NEW ANTIBACTERIAL COMPOUNDS

The present invention relates to novel antibacterial compounds, pharmaceutical compositions containing them and their use as antimicrobials.

Tyrosinase inhibitor, preparation method and uses thereof

The present invention discloses an oxime ether group-containing hydroxypyridone derivative having tyrosinase inhibition activity. The preparation method comprises that the site 5 hydroxy of kojic acid is benzylated, the benzylated kojic acid reacts with a

Preparation method and uses of multifunctional hydroxypyridone derivative and hydrate thereof

The invention discloses a multifunctional hydroxypyridone derivative and a hydrate thereof. The preparation method comprises that the site 5 hydroxy of kojic acid is benzylated, the benzylated kojic acid reacts with ammonia water, the site 2 hydroxymethyl

Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors

Two groups of novel hydroxypyridinone derivatives 6(a-e) and 12(a-c), were designed as potential tyrosinase inhibitors, and synthesized using kojic acid as a starting material. The tyrosinase inhibitory activity of these two groups was demonstrated to be potent, especially compounds 6e and 12a, whose IC50 values for monophenolase activity were 1.95 μM and 2.79 μM, respectively. Both of these values are lower than that of kojic acid (IC50 = 12.50 μM). Compounds 6e and 12a were investigated for the inhibitory effect on diphenolase activity. The results showed that the inhibitory mechanism of these two compounds was reversible and that the inhibitory type was a competitive-uncompetitive mixed-type. The values of IC50 of 6e and 12a on the diphenolase activity of tyrosinase were determined to be 8.97 μM and 26.20 μM, respectively. The inhibitory constants (KI and KIS) of 6e were determined as 17.17 μM and 22.09 μM, respectively; and the KI and KIS values of 12a were 34.41 μM and 79.02 μM, respectively. Compound 6e showed a greater ability to reduce copper and a stronger copper chelating ability than kojic acid.

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.