1219-33-6

Usage

Uses

Used in Pharmaceutical Development:
5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid is used as a key intermediate in the synthesis of pharmaceutical drugs due to its unique structure and properties, which can be leveraged to develop new therapeutic agents with specific biological activities.
Used in Organic Synthesis:
In the field of organic synthesis, 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid is used as a building block for the creation of other chemical compounds, contributing to the development of novel molecules with potential applications in various industries.
Used in Medicinal Chemistry Research:
5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid is utilized in medicinal chemistry research to explore its potential as a precursor for the development of new drugs, taking advantage of its structural features to design molecules with improved pharmacological properties.
Used in Chemical Compound Design:
In the design of chemical compounds, 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid is employed as a versatile component that can be modified and combined with other chemical entities to create new molecules with specific functions and applications in various scientific and industrial fields.

Upstream product

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

Downstream Products

• 61049-67-0 3-Benzyloxy-4-pyrone 
• 496-63-9 3-hydroxy-pyran-4-one 
• 742026-59-1 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid 
• 862389-82-0 7-(Benzyloxy)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione 
• 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 
• 362598-71-8 3-benzyloxy-1-(2-morpholin-4-yl-ethyl)-1H-pyridin-4-one 
• 362598-68-3 3-benzyloxy-1-(2-piperidin-1-yl-ethyl)-1H-pyridin-4-one 
• 119736-19-5 2-Pyridinecarboxylic acid, 1,4-dihydro-1-methyl-4-oxo-5-(phenylmethoxy)- 
• 16494-79-4 3-hydroxy-1-phenyl-1H-pyridin-4-one 
• 499-78-5 comenic acid 
• 1333329-01-3 3-hydroxy-3'-phenyl-4H-1,2'-bipyridin-4-one 
• 1333328-92-9 3-hydroxy-4'-phenyl-4H-1,2'-bipyridin-4-one 
• 1333329-88-6 3'-fluoro-3-hydroxy-4'-phenyl-4H-1,2'-bipyridin-4-one 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel DNA gyrase inhibitors and their siderophore mimic conjugates

Bacterial DNA gyrase is an important target for the development of novel antibacterial drugs, which are urgently needed because of high level of antibiotic resistance worldwide. We designed and synthesized new 4,5,6,7-tetrahydrobenzo[d]thiazole-based DNA gyrase B inhibitors and their conjugates with siderophore mimics, which were introduced to increase the uptake of inhibitors into the bacterial cytoplasm. The most potent conjugate 34 had an IC50 of 58 nM against Escherichia coli DNA gyrase and displayed MIC of 14 μg/mL against E. coli ΔtolC strain. Only minor improvements in the antibacterial activities against wild-type E. coli in low-iron conditions were seen for DNA gyrase inhibitor – siderophore mimic conjugates.

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.

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.

5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid preparation method

The present invention discloses a 5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid preparation method comprising the following steps: adding kojic acid, benzyl chloride and methanol benzyl chloride into a reaction vessel, and heating for reflux reaction for 16 to 18 hours; distilling under reduced pressure, evaporating the solvent to dryness, and cooling to room temperature; adding methanol and water, stirring, washing, filtering and drying to obtain an intermediate; and adding the intermediate and water into the reaction vessel, reducing the temperature to 0 DEG C to -10 DEG C, adding sodium periodate, controlling the temperature to be not higher than 5 DEG C, then adding dropwise a proper amount of water, stirring for 5-15 minutes, heating to 12 DEG C-22 DEG C, stirring for reaction for 2.5 to 3.5 hours, extracting with ethyl acetate, layering, drying, filtering and drying to obtain white solid 5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid. The new 5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid preparation method is provided, does not produce large amounts of chromium-containing waste water, prevents severe environmental pollution, and can achieve industrial production.

Synthesis and evaluation of heterocyclic catechol mimics as inhibitors of catechol-o-methyltransferase (COMT)

3-Hydroxy-4-pyridinones and 5-hydroxy-4-pyrimidinones were identified as inhibitors of catechol-O-methyltransferase (COMT) in a high-throughput screen. These heterocyclic catechol mimics exhibit potent inhibition of the enzyme and an improved toxicity profile versus the marketed nitrocatechol inhibitors tolcapone and entacapone. Optimization of the series was aided by X-ray cocrystal structures of the novel inhibitors in complex with COMT and cofactors SAM and Mg2+. The crystal structures suggest a mechanism of inhibition for these heterocyclic inhibitors distinct from previously disclosed COMT inhibitors.

Pyridone-conjugated monobactam antibiotics with gram-negative activity

Herein we describe the structure-aided design and synthesis of a series of pyridone-conjugated monobactam analogues with in vitro antibacterial activity against clinically relevant Gram-negative species including Pseudomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli. Rat pharmacokinetic studies with compound 17 demonstrate low clearance and low plasma protein binding. In addition, evidence is provided for a number of analogues suggesting that the siderophore receptors PiuA and PirA play a role in drug uptake in P. aeruginosa strain PAO1.

MONOBACTAMS

The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.

Preparation, gram-negative antibacterial activity, and hydrolytic stability of novel siderophore-conjugated monocarbam diols

A novel series of monocarbam compounds exhibiting promising antibacterial activity against multidrug resistant Gram-negative microorganisms is reported, along with the synthesis of one such molecule MC-1 (1). Also reported are structure-activity relationships associated with the in vitro and in vivo efficacy of 1 and related analogues in addition to the hydrolytic stability of such compounds and possible implications thereof.

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