3749-51-7

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dihydroxy-6-methylpyridine is used as a synthetic intermediate for the development of p38 kinase inhibitors. These inhibitors play a crucial role in managing and treating a range of inflammatory diseases and conditions by targeting the p38 kinase enzyme, which is involved in the regulation of cellular responses to stress and inflammation.
Additionally, 2,4-Dihydroxy-6-methylpyridine is utilized in the synthesis of Favipucine analogs. Favipucine is an antimicrobial and fungicidal agent, and its analogs are developed to enhance the effectiveness against various microbial infections, including bacterial and fungal pathogens. This application is particularly relevant in the field of medicine and pharmaceuticals, where the continuous development of new antimicrobial agents is essential to combat drug-resistant infections.

InChI:InChI=1/C6H7NO2/c1-4-2-5(8)3-6(9)7-4/h2-3H,1H3,(H2,7,8,9)

Upstream product

• 856834-08-7 2,4-diethoxy-6-methyl-pyridine 
• 10350-10-4 ethyl 2,4-dihydroxy-6-methylnicotinate 
• 520-45-6 Dehydracetic acid 
• 42779-56-6 2,4-dichloro-6-methyl-pyridine 
• 3749-51-7 4-hydroxy-6-methyl-2-pyridone 
• 130473-38-0 2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one 
• 1332372-75-4 C₉H₁₃NO₃ 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 541-98-0 6-methyl-pyran-2,4-dione 
• 7647-01-0 hydrogenchloride 
• 67-64-1 acetone 
• 100-46-9 benzylamine 

Downstream Products

• 79055-52-0 2,4-dibromo-6-methylpyridine 
• 42779-56-6 2,4-dichloro-6-methyl-pyridine 
• 58096-00-7 6-methyl-4-(N'-phenyl-hydrazino)-pyridin-2-ol 
• 59225-86-4 4,7-dimethyl-6H-pyrano[3,2-c]pyridine-2,5-dione 
• 59225-87-5 2,7-dimethyl-6H-pyrano[3,2-c]pyridine-4,5-dione 
• 40334-96-1 2,4-dimethoxy-6-methyl-pyridine 
• 40334-98-3 2-Methoxy-1,6-dimethyl-4-pyridone 
• 72982-87-7 4-Methoxy-6-methyl-2-pyridone 
• 74990-57-1 4-(3-chloro-anilino)-6-methyl-1H-pyridin-2-one 
• 193888-02-7 ethyl 2-amino-5,6-dihydro-7-methyl-5-oxo-4-phenyl-4H-pyrano[3,2-c]pyridine-3-carboxylate 
• 54885-28-8 4-Hydroxy-6-methyl-3-(2-nitrophenylthio)-2(1H)-pyridon 
• 4966-90-9 4-hydroxy-6-methyl-3-nitro-2(1H)-pyridinone 
• 955377-04-5 C₁₅H₁₁NO₄ 
• 54885-42-6 4-hydroxy-6-methyl-3-phenylsulfinyl-2(1H)-pyridone 

Relevant academic research and scientific papers

Structural and electronic modifications of pyridones and pyrones via regioselective bromination and trifluoromethylation

We report regioselective functionalization of pyridones and pyrones via electrophilic bromination (Br2) or radical trifluoromethylation (NaSO2CF3/tBuOOH) at the 3-position. Counter-intuitively, the 3-position EW groups decreased the carbonyl stretching energy by 6–23 cm?1; however, 3,5-dibromination increased the C[dbnd]O frequency by 10–22 cm?1 compared to the 3-Br pyridones. X-ray crystallography revealed pyridone tautomers with contracted C[dbnd]O bond metrics. pKa values and 1H NMR shifts for the series 3-H→Br→CF3 revealed the expected trend of increasing acidity (pKa = 8.85 → 8.33→6.78, MeOH) and increasing chemical shifts (10.97 → 11.42→11.71 DMSO-d6). We conclude that the paradoxical decrease in CO stretching frequencies by the 3-positoin EW groups is explained by an ‘assistive’ electron-withdrawing effect, whereby the 3-position EW group assists the electronegative oxygen atom in recruiting more electron density, and – as a result – attaining more oxyanion character (decreased the C[dbnd]O bond strength).

Synthesis and characterization of some hydroxypyridone derivatives and their evaluation as antimicrobial agents

The synthesis, in vitro antimicrobial activities of some novel hydroxy pyridines supported with various pharmacophores is described. Twenty-six out of the tested 58 compounds exhibited variable inhibitory effects on the growth of the tested Gram positive

Production of Piperidine and δ-Lactam Chemicals from Biomass-Derived Triacetic Acid Lactone

Piperidine and δ-Lactam chemicals have wide application, which are currently produced from fossil resource in industry. Production of this kind of chemicals from lignocellulosic biomass is of great importance, but is challenging and the reported routes gi

COUMARIN-LIKE CYCLIC COMPOUND AS MEK INHIBITOR AND USE THEREOF

Disclosed are a class of coumarin-like cyclic compounds as MEK inhibitors and pharmaceutical compositions comprising the compounds, and the use of same in the preparation of a drug for treating MEK-related diseases. Particularly disclosed are compounds as shown in formula (I) and pharmaceutically acceptable salts thereof or tautomers thereof.

Design, Synthesis, and Phenotypic Profiling of Pyrano-Furo-Pyridone Pseudo Natural Products

Natural products (NPs) inspire the design and synthesis of novel biologically relevant chemical matter, for instance through biology-oriented synthesis (BIOS). However, BIOS is limited by the partial coverage of NP-like chemical space by the guiding NPs. The design and synthesis of “pseudo NPs” overcomes these limitations by combining NP-inspired strategies with fragment-based compound design through de novo combination of NP-derived fragments to unprecedented compound classes not accessible through biosynthesis. We describe the development and biological evaluation of pyrano-furo-pyridone (PFP) pseudo NPs, which combine pyridone- and dihydropyran NP fragments in three isomeric arrangements. Cheminformatic analysis indicates that the PFPs reside in an area of NP-like chemical space not covered by existing NPs but rather by drugs and related compounds. Phenotypic profiling in a target-agnostic “cell painting” assay revealed that PFPs induce formation of reactive oxygen species and are structurally novel inhibitors of mitochondrial complex I.

Small molecule inhibitors of anthrax edema factor

Anthrax is a highly lethal disease caused by the Gram-(+) bacteria Bacillus anthracis. Edema toxin (ET) is a major contributor to the pathogenesis of disease in humans exposed to B. anthracis. ET is a bipartite toxin composed of two proteins secreted by the vegetative bacteria, edema factor (EF) and protective antigen (PA). Our work towards identifying a small molecule inhibitor of anthrax edema factor is the subject of this letter. First we demonstrate that the small molecule probe 5′-Fluorosulfonylbenzoyl 5′-adenosine (FSBA) reacts irreversibly with EF and blocks enzymatic activity. We then show that the adenosine portion of FSBA can be replaced to provide more drug-like molecules which are up to 1000-fold more potent against EF relative to FSBA, display low cross reactivity when tested against a panel of kinases, and are nanomolar inhibitors of EF in a cell-based assay of cAMP production.

Discovery of Multitarget Antivirals Acting on Both the Dengue Virus NS5-NS3 Interaction and the Host Src/Fyn Kinases

This study describes the discovery of novel dengue virus inhibitors targeting both a crucial viral protein-protein interaction and an essential host cell factor as a strategy to reduce the emergence of drug resistance. Starting from known c-Src inhibitors

Synthesis of 6-substituted-4-hydroxy-2-pyridinones via intramolecular ketene trapping of functionalized enamine-dioxinones

The synthesis of various 6-substituted-4-hydroxy-2-pyridinones is reported. The functionalized keto-dioxinones were constructed via a diethylzinc mediated crossed Claisen condensation reaction and subsequent enamine formation, thermolysis, and cyclization

FURANOPYRIDINE CANNABINOID COMPOUNDS AND RELATED METHODS OF USE

Furanopyridine cannabinoid analog compounds of the formula (I) are disclosed. The compounds are useful to modify the activity of CB 1 and CB2 receptors and treat conditions mediated by these receptors.

Synthesis and phytotoxic activity of new pyridones derived from 4-hydroxy-6-methylpyridin-2(1H)-one

Commercial dehydroacetic acid was converted into 4-hydroxy-6-methylpyridin- 2(1 H)-one (3), which was then condensed with several aliphatic aldehydes to produce seven new title compounds in variable yields (35-92%). Reaction of 3 with α,β-unsaturated aldehydes resulted in the formation of condensed pyran derivatives 4g′ and 4h′. A mechanism is proposed to explain the formation of such compounds. The effects of all methylpyridin-2(1 H)-one derivatives on the development of the dicotyledonous species Ipomoea grandifolia and Cucumis sativus and the monocotyledonous species Sorghum bicolor were evaluated. At the dose of 6.7 × 10-8 mol a.i./g substrate the compounds showed some phytotoxic selectivity, being more active against the dicotyledonous species. These compounds can be used as lead structures for the development of more active phytotoxic products.