Regiospecific Reduction of the C=N Bond in 5,6-Dialkyl-2-Chloropyridine-3,4-Dicarbonitriles

Ершов, О. В.; Belikov, М. Yu.; Максимова, В. Н.; Федосеев, С. В.; Legotin, Sergey; Насакин, О. Е.

doi:10.1007/s10593-014-1564-6

Cited by 7 publications

(2 citation statements)

References 12 publications

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“…Pyridines are among the most important biochemical scaffolds with broader uses in the medicinal and pharmaceutical industries as well as intermediates in heterocyclic preparations . Among pyridine derivatives, dicyanopyridines act as ‘privileged skeleton’ owing to their prospective uses for therapy . These derivatives were recorded to serve as anti‐prion, human adenosine A2B receptor, antibacterial, anti‐cancer, and anti‐hepatitis B virus .…”

Section: Background and Originality Contentmentioning

confidence: 99%

“…A variety of 2‐chloropyridine‐3,4‐dicarbonitrile derivatives is accessible and could be prepared from 4‐oxoalkane‐1,1,2,2‐tetracarbonitriles in the existence of aqueous HCl or in dry HCl (acetyl chloride/ propan‐2‐ol) . Comparable protocols for the assembly of 2‐chloropyridine‐3,4‐dicarbonitriles have also been reported via a one‐pot three‐component reaction of tetracyanoethylene (TCNE) and HCl with several ketones . Some of these strategies involve one or more drawbacks such as prolonged processes, harsh conditions, waste production, hazardous solvents, elevated temperature, and poor yields of products.…”

Section: Background and Originality Contentmentioning

confidence: 99%

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Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Arafa

Hussein

2020

Chin. J. Chem.

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of main observation and conclusion A highly efficient, simple, and clean single-step sonosynthetic procedure has been sophisticated for assembling new series of mono-and bis-pyridine dicarbonitriles from ketones, HCl, and tetracyanoethylene. The presented protocol is applicable for the preparation of a broad range of uniquely substituted pyridine dicarbonitriles and seems to be superior in comparison with other previously reported methods. The antiproliferative impact of the newly synthesized derivatives was screened towards three representative cancer cell lines (MCF-7, A549, and HCT116). Most of the evaluated derivatives showed a moderate to excellent anti-proliferative activity towards the selected cell lines. Of these, compounds 4h, 4k, 10, 12a, and 12b showed both potent anticancer activity (IC50<10 μM) and lower cytotoxic effect (IC50 > 58 μM) on non-tumorigenic cells (MCF-10A and NCM460), suggesting their promising potential to be lead molecules for future antitumor drug discovery. The structure-activity relationships have been also discussed. Moreover, quantum chemical studies based on Density Functional Theory (DFT) of the synthesized compounds were investigated and found to be consistent with the in vitro inhibitory activities. Results and DiscussionPreparation of 6-chloro-[2,2'-bipyridine]-4,5-dicarbonitrile (4a) by treatment of tetracyanoethylene (1, TCNE, 1.0 mmol), and 2-acetyl pyridine (2a, 1.0 mmol) with HCl (3.0 mL) was chosen as the template reaction (Scheme 1) under silent (70 o C) and ultra-502 www.cjc.wiley-vch.de

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Section: Background and Originality Contentmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Arafa

Hussein

2020

Chin. J. Chem.

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ChemInform Abstract: Regiospecific Reduction of the C=N Bond in 5,6‐Dialkyl‐2‐chloropyridine‐3,4‐dicarbonitriles.

et al. 2015

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A General Synthesis of Dihydronaphthyridinones with Aryl-Substituted Quaternary Benzylic Centers

2023

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A variety of 7,8-dihydro-1,6-naphthyridin-5(6H)-ones and 3,4-dihydro-2,7-naphthyridin-1(2H)-ones with quaternary centers and aryl substitutions at the benzylic carbon were synthesized with a new 3-step, 2-pot method. The first step is an SNAr using widely available 2- and 4-chloronicotinate esters and tertiary benzylic nitriles. The last two steps are a one-pot selective nitrile reduction in the presence of various heterocycles followed by a lactam ring closure of the free amine on the ester.

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Regiospecific Reduction of the C=N Bond in 5,6-Dialkyl-2-Chloropyridine-3,4-Dicarbonitriles

Cited by 7 publications

References 12 publications

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

ChemInform Abstract: Regiospecific Reduction of the C=N Bond in 5,6‐Dialkyl‐2‐chloropyridine‐3,4‐dicarbonitriles.

A General Synthesis of Dihydronaphthyridinones with Aryl-Substituted Quaternary Benzylic Centers

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