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3-Cyano-4,6-dimethyl-2-hydroxypyridine is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

769-28-8

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769-28-8 Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 2616, 1951 DOI: 10.1021/ja01150a057

Check Digit Verification of cas no

The CAS Registry Mumber 769-28-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 9 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 769-28:
(5*7)+(4*6)+(3*9)+(2*2)+(1*8)=98
98 % 10 = 8
So 769-28-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H8N2O/c1-5-3-6(2)10-8(11)7(5)4-9/h3,7H,1-2H3/t7-/m1/s1

769-28-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A12466)  3-Cyano-2-hydroxy-4,6-dimethylpyridine, 98%   

  • 769-28-8

  • 5g

  • 318.0CNY

  • Detail
  • Alfa Aesar

  • (A12466)  3-Cyano-2-hydroxy-4,6-dimethylpyridine, 98%   

  • 769-28-8

  • 25g

  • 1445.0CNY

  • Detail
  • Alfa Aesar

  • (A12466)  3-Cyano-2-hydroxy-4,6-dimethylpyridine, 98%   

  • 769-28-8

  • 100g

  • 4923.0CNY

  • Detail
  • Aldrich

  • (C90801)  2-Hydroxy-4,6-dimethylpyridine-3-carbonitrile  98%

  • 769-28-8

  • C90801-5G

  • 409.50CNY

  • Detail
  • Aldrich

  • (C90801)  2-Hydroxy-4,6-dimethylpyridine-3-carbonitrile  98%

  • 769-28-8

  • C90801-5G

  • 409.50CNY

  • Detail
  • Aldrich

  • (C90801)  2-Hydroxy-4,6-dimethylpyridine-3-carbonitrile  98%

  • 769-28-8

  • C90801-5G

  • 409.50CNY

  • Detail
  • Aldrich

  • (C90801)  2-Hydroxy-4,6-dimethylpyridine-3-carbonitrile  98%

  • 769-28-8

  • C90801-5G

  • 409.50CNY

  • Detail

769-28-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Cyano-4,6-Dimethyl-2-Hydroxypyridine

1.2 Other means of identification

Product number -
Other names 3-Cyano-4,6-dimethyl-2-hydroxypyridine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:769-28-8 SDS

769-28-8Relevant articles and documents

Kinetics and Mechanism of the Condensation Reaction of Symmetrical and Unsymmetrical 1,3-Diketones with Cyanoacetamide in the Synthesis of 4,6-Disubstituted-3-cyano-2-pyridones

Misic-Vukovic, Milica,Radojkovic-Velickovic, Mirjana

, p. 1965 - 1970 (1992)

The rate constants for the condensation of cyanoacetamide with pentane-2,4-dione, 5-methylhexane-2,4-dione and 5,5-dimethylhexane-2,4-dione catalysed by piperidine were determined under a variety of experimental conditions.A UV spectrophotometric method for rate measurements was developed and the structures of the products were elucidated by means of a spectroscopic study.On the basis of the obtained rate constants, activation parameters and the evidence on the structure of synthesized unsymmetrical 4,6-disubstituted-3-cyano-2-pyridones a possible reaction scheme was suggested.It was thus possible to explain the selectivity of the reaction and the position of substituents in the pyridones obtained.

An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions

Kazemi, Bagher,Javanshir, Shahrzad,Maleki, Ali,Safari, Mostafa,Khavasi, Hamid Reza

, p. 6977 - 6981 (2012)

A new and efficient method has been developed for the synthesis of highly functionalized 2-amino-4H-pyran, 2-amino-4H-chromene, 2-amino-oxepine, and 2-hydroxy-oxepine derivatives through one-pot, three-component tandem reactions of structurally diverse 1,3-diketones, dialkyl acetylenedicarboxylates, and malononitrile or ethyl cyanoacetate in the presence of a catalytic amount of Na2CO3 in ethanol. This efficient technique has the advantages of giving products in good to high yields, in short reaction times, and with a simple isolation procedure.

An Unusual Photodimerisation of a Pyrone Analogue; X-Ray Crystal Structure of the Principal Product

Alcock, Nathaniel W.,Samuel, Christopher J.

, p. 603 - 604 (1982)

Irradiation of 4-dicyanomethylene-2,6-dimethyl-4H-pyran (1) in methanol leads to the dimers (2) and (3); the structure of (2) has been determined by X-ray crystallography.

Synthesis and halocyclization of 3-cyano-4,6-dimethyl-2-pyridone allyl derivatives

Kim, Dmitry G.,Kalita, Elena V.,Sharutin, Vladimir V.,Ovchinnikova, Irina G.,Ezhikova, Marina А.,Kodess, Mikhail I.,Slepukhin, Pavel А.,Vasilenko, Anna V.

, p. 566 - 572 (2019)

[Figure not available: see fulltext.] The sequence of condensation, alkylation, and halocyclization reactions during the synthesis of the target 2,3-dihydro[1,3]oxazolo[3,2-a]-pyridinium salts was investigated. The effect of basic catalysis on the chemoselectivity of the reaction of malononitrile with acetylacetone has been revealed. In neutral media, the selectivity of the formation of 3-cyano-4,6-dimethyl-2-pyridone increases. The presence of Et3N, on the other hand, leads to the formation of side products. Allylation of 3-cyano-4,6-dimethyl-2-pyridone proceeds with the formation of regioisomeric 1-allyl-3-cyano-4,6-dimethyl-2-pyridone and 2-allyl-3-cyano-4,6-dimethyloxypyridine in a 3:1 ratio, while the high chemoselectivity of halocyclization of allyl derivatives with iodine or bromine results in practically quantitative yields of 2,3-dihydro[1,3]oxazolo[3,2-a]pyridinium salts.

Synthesis, physicochemical and vibrational spectral properties of 2–pyridone and 2–aminopyridine derivatives: An experimental and theoretical study

El–Tahawy, Mohsen M. T.,Garavelli, Marco,Keshk, Reda M.

, (2020/09/01)

A convenient and efficient one–pot three–component reaction of acetyl acetone, malononitrile and ammonium acetate was investigated for the synthesis of 3–cyano–4,6–dimethyl–2–pyridone (PI) and 2–amino–3–cyano–4,6–dimethylpyridine (PII). The products were achieved with high purity, high yields and short reaction time. The yields of the two products depend on the concentration of ammonium acetate, reaction time and the solvent used. The structures of the isolated products were confirmed by elemental analysis and spectral data, supported by quantum chemical (MP2) calculations, both in gas phase and solvents (water and ethanol), that were also employed to track the reaction mechanisms and model vibrational spectral properties for final characterization and interpretation of spectral data. A remarkable matching between theoretical predictions and experiments was attained both for the geometrical parameters, as compared to X-Ray data available in the literature, and for vibrational frequencies, leading to a correlation coefficient (R2) of 0.99. Molecular docking was further studied to predict the docking binding energy of the synthesized compounds with the target proteins.

Discovery of quinolone derivatives as antimycobacterial agents

Gao, Chao,Li, Xiao,Liu, Kun-Lin,Teng, Fei,Xiong, Lu,Yu, Luo-Ting

, p. 24095 - 24115 (2021/07/29)

Tuberculosis (TB), an infectious disease caused byMycobacterium tuberculosis(M. tuberculosis), is an important public health issue. Current first-line drugs administered to TB patients have been in use for over 40 years, whereas second-line drugs display strong side effects and poor compliance. Additionally, designing effective regimens to treat patients infected with multi- and extremely-drug-resistant (MDR and XDR) strains of TB is challenging. In this report, we screened our compound library and identified compound1with antituberculosis activity and a minimal inhibitory concentration (MIC) againstM. tuberculosisof 20 μg mL?1. Structure optimization and the structure-activity relationship of1as the lead compound enabled the design and synthesis of a series of quinolone derivatives,6a1-6a2,6b1-6b36,6c1,6d1-6d14,7a1-7a2,7b1-7b2,7c1,8a1-8a5,9a1-9a4and10a1-10a6. These compounds were evaluatedin vitrofor anti-tubercular activity against theM. tuberculosisH37Rv strain. Among them, compounds6b6,6b12and6b21exhibited MIC values in the range of 1.2-3 μg mL?1and showed excellent activity against the tested MDR-TB strain (MIC: 3, 2.9 and 0.9 μg mL?1, respectively). All three compounds were non-toxic toward A549 and Vero cells (>100 and >50 μg mL?1, respectively). In addition, an antibacterial spectrum test carried out using compound6b21showed that this compound specifically inhibitsM. tuberculosis. These can serve as a new starting point for the development of anti-TB agents with therapeutic potential.

1,5,7-TRISUBSTITUTED ISOQUINOLINE DERIVATIVES, PREPARATION THEREOF, AND USE THEREOF IN MEDICINES

-

Paragraph 0210-0211; 0224-0225, (2020/08/30)

The present disclosure relates to 1,5,7-trisubstituted isoquinoline derivatives, their preparation and pharmaceutical use. In particular, the present disclosure discloses a compound of formula (I) or a pharmaceutically acceptable salt, stereoisomer, solvate or prodrug thereof, and a preparation method and use thereof. The definitions of the groups in the formula can be found in the specification and claims.

Synthesis and Photophysical Properties of 3-Amino-4-arylpyridin-2(1 H)-ones

Abramov, Anton A.,Chernenko, Sergey A.,Fisyuk, Alexander S.,Kostyuchenko, Anastasia S.,Shatsauskas, Anton L.

, p. 227 - 238 (2019/12/28)

A method has been developed for the preparation of oxazolo-[5,4- b ]pyridin-2(1 H)-ones based on the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides. Hydrolysis of oxazolo[5,4- b ]pyridin-2(1 H)-ones and the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides yielded 3-aminopyridin-2(1 H)-ones, including 4-aryl substituted derivatives in the series, for which effective phosphors with a quantum yield of up to 0.78 were detected. Photophysical properties of 3-aminopyridin-2(1 H)-ones were studied by UV and luminescence spectroscopy methods, and the relationship between their structure and photophysical properties was revealed.

5-Hydroxyindole-based EZH2 inhibitors assembled via TCCA-catalyzed condensation and Nenitzescu reactions

Chen, Guoliang,Du, Fangyu,Sun, Wenjiao,Wang, Lihui,Wu, Chunfu,Yang, Cheng,Zhou, Qifan

supporting information, (2020/05/16)

5-Hydroxyindole derivatives have various demonstrated biological activities. Herein, we used 5-hydroxyindole as a synthetic starting point for structural alterations in a combinatorial process to synthesize 22 different compounds with EZH2 inhibitor pharmacophores. A series of 5-hydroxyindole-derived compounds were screened inhibitory activities against K562 cells. According to molecular modeling and in vitro biological activity assays, the preliminary structure-activity relationship was summarized. Compound L–04 improved both the H3K27Me3 reduction and antiproliferation parameters (IC50 = 52.6 μM). These findings revealed that compound L–04 is worthy of consideration as a lead compound to design more potent EZH2 inhibitors. During the preparation of compounds, we discovered that trichloroisocyanuric acid (TCCA) is a novel catalyst which demonstrates condensation-promoting effects. To gain insight into the reaction, in situ React IR technology was used to confirm the reactivity. Different amines were condensed in high yields with β-diketones or β-ketoesters in the presence of TCCA to afford the corresponding products in a short time (10~20 min), which displayed some advantages and provided an alternative condensation strategy.

Design, synthesis and biological activities of pyrrole-3-carboxamide derivatives as EZH2 (enhancer of zeste homologue 2) inhibitors and anticancer agents

Zhou, Qifan,Jia, Lina,Du, Fangyu,Dong, Xiaoyu,Sun, Wanyu,Wang, Lihui,Chen, Guoliang

supporting information, p. 2247 - 2255 (2020/02/20)

Zeste enhancer homolog 2 (EZH2) is highly expressed in various malignant tumors, which could silence tumor suppressor genes via trimethylation of H3K27. Herein was first reported a novel series of pyrrole-3-carboxamide derivatives carrying a pyridone fragment as EZH2 inhibitors. By combining computational modeling, in vitro cellular assays and further rational structure-activity relationship exploration and optimization, compound DM-01 showed powerful inhibition towards EZH2. DM-01 was found to have significant ability to reduce the cellular H3K27me3 level in K562 cells in the Western blot test. Meanwhile, our data showed that knockdown EZH2 in A549 cells resulted in a decrease of cell sensitivity to DM-01 at 50 and 100 μM. DM-01 could also increase the transcription expression of DIRAS3 in a dose-dependent manner, a tumor suppressor in the downstream of EZH2, suggesting it was worth investigating further as a lead compound.

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