6266-91-7

Upstream product

• 54917-86-1 5-acetoxy-2-methyl-pyran-4-one 
• 74-88-4 methyl iodide 
• 6269-25-6 2-Hydroxymethyl-5-methoxy-4H-pyran-4-on 
• 7559-81-1 chlorokojic acid 
• 644-46-2 allomaltol 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 40838-34-4 2-chloromethyl-5-methoxy-4H-pyran-4-one 

Downstream Products

• 62885-48-7 4,5-Dimethoxy-2-methyl-pyridin 
• 1333329-07-9 1-biphenyl-3-yl-5-hydroxy-2-methylpyridin-4(1H)-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.

Design, synthesis and biological evaluation of hydroxypyridinone-coumarin hybrids as multimodal monoamine oxidase B inhibitors and iron chelates against Alzheimer's disease

A series of hybrids of hydroxypyridinone and coumarin were rationally designed, synthesized and biologically evaluated for their iron ion chelating and MAO-B inhibitory activities. Most of the compounds displayed excellent iron ion chelating effects and moderate to good anti-MAO-B activities. Compound 27a exhibited the most potent activity against MAO-B, with an IC50 value of 14.7 nM. Importantly, 27a showed good U251 cell protective effect and significantly ameliorated the cognitive dysfunction of scopolamine-induced AD mice. Moreover, molecular docking was performed to elucidate the probable ligand-receptor interaction, and the structure-activity relationships were also summarized.

Synthetic method for amino-containing hydroxypyridone compound

The invention discloses a synthetic method for an amino-containing 3-hydroxypyridine-4-ketone iron chelating agent as shown in a formula (III) which is described in the specification. The synthetic method comprises the following steps: with methyl-protected azido hydroxypyridone as shown in a formula (I) which is described in the specification as a raw material, allowing the methyl-protected azido-hydroxypyridine to generate reduction and demethylation reactions under the protection of boron tribromide as shown in a formula (II) which is described in the specification, a solvent A and gas B, after completion of the reactions, carrying out quenching with a solvent C, and carrying out post-treatment so as to obtain the amino-containing 3-hydroxypyridine-4-ketone compound as shown in the formula (III). Compared with a conventional method, the synthetic method provided by the invention adopts a boron tribromide reagent with mild reaction conditions, avoids the use of a metal catalyst, andhas simple and convenient operation and high reaction yield.

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.

'Unconventional' coordination chemistry by metal chelating fragments in a metalloprotein active site

The binding of three closely related chelators: 5-hydroxy-2-methyl-4H- pyran-4-thione (allothiomaltol, ATM), 3-hydroxy-2-methyl-4H-pyran-4-thione (thiomaltol, TM), and 3-hydroxy-4H-pyran-4-thione (thiopyromeconic acid, TPMA) to the active site of human ca

Direct C3-alkenylation of pyridin-4(1H)-one via oxidative Heck coupling

Oxidative Heck coupling of pyridin-4(1H)-one via palladium(II)-catalyzed C-H bond activation has been achieved in moderate to good yields. The coupling occurred selectively at C3 position. Pivalic acid was found to be an effective additive to promote this

Re-examination of nucleophilic substitution in chlorokojic acid

Chlorokojic acid was reacted with S2O23 , NO-3 , N-3 , I- , and SCN- . Only the three latter nucleophiles substituted the chlorine atom in the 2-CH2/s