5444-02-0

Basic information

• Product Name: 3-Cyano-2,6-dihydroxy-4-methylpyridine
• Synonyms: 1,2-dihydro-6-hydroxy-4-methyl-2-oxo-3-pyridinecarbonitril;2,6-DIHYDROXY-4-METHYL-3-PYRIDINECARBONITRILE;2,6-DIHYDROXY-3-CYANO-4-METHYLPYRIDINE;2,6-DIHYDROXY-4-METHYLNICOTINONITRILE;2,6-DIHYDROXY-4-METHYLPYRIDINE-3-CARBONITRILE;3-CYANO-2,6-DIHYDROXY-4-METHYLPYRIDINE;1,2-dihydro-6-hydroxy-4-methyl-2-oxonicotinonitrile;2,6-Dihydroxy-4-methyl-3-piridinecarbonitrile
• CAS NO: 5444-02-0
• Molecular Formula: C₇H₆N₂O₂
• Molecular Weight: 150.13
• EINECS: 226-639-7
• Product Categories: Intermediates of Dyes and Pigments;Heterocyclic Compounds;Pyridines;Alcohols;Monomers;Polymer Science;alcohol|cyanide
• Mol File: 5444-02-0.mol

Chemical Properties

• Melting Point: 315 °C (dec.)(lit.)
• Boiling Point: 323 °C at 760 mmHg
• Flash Point: 149.1 °C
• Appearance: /
• Density: 1.38 g/cm³
• Vapor Pressure: 0.116mmHg at 25°C
• Refractive Index: 1.491
• PKA: 3.59±0.58(Predicted)
• CAS DataBase Reference: 3-Cyano-2,6-dihydroxy-4-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyano-2,6-dihydroxy-4-methylpyridine(5444-02-0)
• EPA Substance Registry System: 3-Cyano-2,6-dihydroxy-4-methylpyridine(5444-02-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5444-02-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Cyano-2,6-dihydroxy-4-methylpyridine is used as an inhibitor for human uridine phosphorylase-1, contributing to its application in the development of treatments for certain diseases. It is particularly effective in reducing HepG2 cell proliferation through cell cycle arrest and senescence, making it a promising candidate for cancer research and therapeutics.
Used in Chemical Industry:
3-Cyano-2,6-dihydroxy-4-methylpyridine is used as a key intermediate in the synthesis of disperse dyes. Its unique chemical structure allows for the creation of dyes with specific properties, making it valuable in the production of various colorants for different applications.
Used in Research and Development:
In the field of research and development, 3-Cyano-2,6-dihydroxy-4-methylpyridine is utilized in the synthesis of mGluR5 non-competitive antagonists. These compounds are essential for studying the role of mGluR5 receptors in various neurological and psychiatric disorders, potentially leading to the development of new treatments for conditions such as anxiety, depression, and chronic pain.

InChI:InChI=1/C9H15NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-5H,6-7H2,1-3H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 105-56-6 ethyl 2-cyanoacetate 
• 107-91-5 cyanoacetic acid amide 
• 105-45-3 acetoacetic acid methyl ester 
• 105-34-0 methyl 2-cyanoacetate 
• 96-34-4 methyl chloroacetate 
• 55212-82-3 ethyl 3-morpholinocrotonate 
• 66003-96-1 β-morpholinoethylcrotonate 
• 73018-20-9 3-oxobutanoic acid 
• 105143-58-6 piperidinium 3-cyano-1,6-dihydro-4-methyl-6-oxo-2-pyridinolate 
• 93272-85-6 3-cyano-6-hydroxy-4-methyl-2(1H)-pyridinethione 
• 105143-58-6 2,6-dihydroxy-3-cyano-4-methylpyridine piperidine salt 
• 110-89-4 piperidine 
• 107-91-5 cyanoacetimide 

Downstream Products

• 4664-16-8 4-methyl-2,6-dihydroxypyridine 
• 26345-14-2 3-cyano-2,6-dimethoxy-4-methylpyridine 
• 38824-75-8 2,6-dibromo-4-methylpyridine-3-carbonitrile 
• 38841-54-2 2,6-dichloro-4-methyl-3-pyridinecarboxamide 
• 129432-25-3 2,6-dichloro-3-amino-4-methylpyridine 

Relevant articles and documents

Continuous flow synthesis of some 6- And 1,6-substituted 3-cyano-4-methyl-2-pyridones

In this study, six 6- and 1,6-substituted-3-cyano-4-methyl-2-pyri-dones were synthesized in a continuous flow microreactor system. The syntheses were realized at room temperature and the obtained results were compared to those achieved within classical syntheses. In order to optimize the continuous flow syntheses and increase the yield of the products, the retention time in the microreactor was varied by changing the flow rates of the reactant solutions. Furthermore, the reaction was optimized for 3-cyano-4,6-dimethyl-2-pyridone and 3-cyano-6-hydroxy-4-methyl-2-pyridone, which are comercially important in the pharmaceutical and dye industries. Both 2-pyridones were obtained in satisfactory yield of circa 60 % in less than 10 min. The resulting compounds were characterized by their melting points, FT-IR, 1H-NMR and UV–Vis spectra. The efficiency of the presented method for the synthesis of 2-pyridone-based molecules has promising potential for industrial production.

Synthesis and thermal properties of arylazo pyridone dyes

Thermal degradation properties of 5-(4-substitutedphenylazo)-3-amido-6-hydroxy-4-methyl-2-pyridones and 5-(4-substitutedphenylazo)-3-cyano-6-hydroxy-4-methyl-2-pyridones dyes, differing in electron withdrawing and electron donating substituents in para-position of diazo components were examined. The structure of the synthesized compounds has been confirmed by 1H NMR,13C NMR, FTIR, UV–Vis and XRD analysis techniques. The results obtained with thermogravimetric analysis (TGA) – derivative thermogravimetry (DTG) and differential thermal analysis (DTA) were combined with GC-mass spectral fragmentation to obtain thermal decomposition mechanism. Non-isothermal kinetics were monitored by application of TGA-DTG-DTA. For Kinetic behavior of the investigated dyes during their degradation in an inert atmosphere, Kissinger, Ozawa, Flynn-Wall-Ozawa (FWO) and Kissinger-Akahira-Sunose (KAS) isoconversional (model-free) methods were applied. It was found that different thermal stabilities of investigated dyes are the consequence of their different chemical structures, including diverse substituents.

NEK6 KINASE INHIBITORS USEFUL FOR THE TREATMENT OF SOLID TUMORS

The mitotic kinases regulating the dynamics of centrosomes and the functions of the mitotic spindle are potential targets for the antitumour therapy. In the present invention some molecules with inhibitory activity on NEK6 have been identified. The present invention relates to such molecules and to the compositions including them for use as inhibitors of NEK6 in a method of treatment of tumours both in monotherapy and in combinations with other drugs.

Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties

New azo dyes bearing 2-pyridone and benzimidazole moieties were prepared using diazotization of 4-(1H-benzo[d]imidazol-2-yl)aniline and coupling of the obtained diazonium salt with substituted 3-cyano-2-pyridones. Obtained compounds were characterized via UV-Vis, FT-IR, and 1 H and 13 C NMR spectroscopy as well as by elemental analysis data. The UV-Vis spectra of the synthesized dyes were measured in thirteen solvents of different properties at room temperature. Solvatochromism and tautomerism of novel azo dyes were discussed. An MTT (3,4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl tetrazolium bromide) test was performed to prove the biocompatibility of the investigated dyes. The investigated dyes exhibited satisfying antiproliferative activities against both tumor cell lines, MDA-MB-231 and HCT-116, demonstrating the potent capacity for treatment of tumors.

Preparation method for nevirapine intermediate

The invention provides a preparation method for a nevirapine intermediate. The preparation method comprises: performing a cyclization reaction of ammonia water, methyl cyanoacetate and methyl acetoacetate to form a compound hydroxyl: 2,6-dihydroxy-3-cyano-4-methylpyridine; adding triethylamine dropwise, introducing chlorine gas at the temperature until the reaction is complete, and obtaining 2,6-dichloro-3-cyano-4-methylpyridine; adding concentrated sulfuric acid, heating to 120 DEG C to react for 3-5 h, and then cooling to 60 DEG C; adding water to perform hydrolysis reaction, and obtaining 2,6-dichloro-3-amido-4-methylpyridine; adding a degradation reagent sodium hypochlorite, and obtaining a nevirapine intermediate 2,6-dichloro-3-amino-4- methylpyridine by Hofmann reaction. According tothe preparation method, commonly used phosphorus oxychloride is replaced with the directly introduced chlorine gas, which solves the problems that the wastewater content is too high, it is difficultto perform treatment and the odor of phosphorus oxychloride is bad, and the one-time yield of the product is 90.1%.

Wnt SIGNALING INHIBITOR, COMPOSITION, AND COMPOUND AS USE THEREFOR

PROBLEM TO BE SOLVED: To provide an inhibitor for Wnt signaling route. SOLUTION: The present invention provides a compound represented by formula I, and a composition comprising the compound (X1-X8 independently represent CR4 or N; Y1 is H or C (R4)3; Y2 and Y3 independently represent H, halogen or C (R3)3; R1 and R2 independently represent H, halogen, C1-6 alkyl, quinolinyl or the like; R3s independently represent H, halogen, cyano, C1-6 alkyl or the like; R4s independently represent H, halogen, cyano, C1-6 alkoxy or the like). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Inhibiting WNT signal conduction of compound, composition and use thereof (by machine translation)

The invention relates to a having the general formula (1) compounds and compositions thereof, and the use of the compound or composition thereof to inhibit WNT signal transmission method. The compounds of this invention and its composition can effectively inhibit the secretion of WNT protein, inhibit WNT signal conduction, so the WNT-mediated disease with a very good therapeutic effect. . (by machine translation)

TUMOR BIOMARKERS AND USE THEREOF

Disclosed herein are biomarkers related to WNT signal transduction pathway, as well as methods and kits comprising the same. Further, the present disclosure relates to the use of the biomarkers in patient selection, companion diagnostics, and treatment of cancer.

Compound as WNT Signaling Inhibitor, Composition, and Use Thereof

The present invention relates to a compound having the structure of Formula I as inhibitor of WNT signal transduction pathways, as well as a composition comprising the compound. Further, the present invention relates to the use of the compound and the method of inhibiting the WNT signal transduction pathways.

AZAINDENOISOQUINOLINE TOPOISOMERASE I INHIBITORS

The invention described herein pertains to substituted azaindenoisoquinoline compounds, in particular 7-, 8-, 9-, and 10-azaindenoisoquinoline compounds, which are inhibitors of topoisomerase I, processes and intermediates for their syntheses, pharmaceutical compositions of the compounds, and methods of using them in the treatment of cancer.