Synthesis, structural, spectroscopic and docking studies of new 5C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles

Vereshchagin, A. N.; Elinson, Michaïl N.; Anisina, Yuliya E.; Ryzhkov, Fedor V.; Goloveshkin, Alexander S.; Новиков, Роман А.; Egorov, Mikhail P.

doi:10.1016/j.molstruc.2017.06.044

Cited by 32 publications

(17 citation statements)

References 24 publications

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“…The resonance occurs in pyridine, pyrazine, and similar sixmembered heterocyclic compounds, allowing the molecule to be planar and stable, much as it does in benzene. Pyridine is peculiar in that it is the azine that is also closest to benzene [1,2,3]. The widespread applicability of the halogen in material science, medical chemistry, molecular recognition processes, catalysis, crystal engineering of halogen bearing compounds and drug design (30-40%) is notable [4].…”

Section: Introductionmentioning

confidence: 99%

Speculative assessment, molecular composition, PDOS, topology exploration (ELF, LOL, RDG), ligand-protein interactions, on 5-bromo-3-nitropyridine-2-carbonitrile

Arulaabaranam

Muthu²,

Mani³

et al. 2021

Heliyon

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Computational calculations of 5-bromo-3-nitropyridine-2-carbonitrile (5B3N2C) on molecular structure and on energy are implemented using the 6-311þþG(d,p) basis set by DFT/B3LYP method. The UV-Vis spectrum of 5B3N2C was obtained by TD-DFT with chloroform as a solvent. The analysis of molecular electrostatic potential (MEP) and frontier molecular orbital (FMO) were used to evaluate, the entire electron density and organic reactive sites of 5B3N2C. The electron-hole conversions were conjointly deliberated. Donor-acceptor interactions (NBO) analysis examines the intra-and intermolecular charge transfer, hyper conjugate interaction of the compound. The orbital molecular contributions are evaluated by density of states (DOS and PDOS). To discern the reactivity of the molecule, topology analyses were done. The biological prominence of the 5B3N2C molecule was investigated in a pertinent study of molecular docking with target protein 3CEJ exhibiting the centromere associated protein inhibitor property. Molecular Dynamics simulations were done to assess the stability of the complex. 5B3N2C physiochemical parameters were also compared to those of widely viable medications Ispinesib and Lonafarnib.

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Section: Introductionmentioning

confidence: 99%

Speculative assessment, molecular composition, PDOS, topology exploration (ELF, LOL, RDG), ligand-protein interactions, on 5-bromo-3-nitropyridine-2-carbonitrile

Arulaabaranam

Muthu²,

Mani³

et al. 2021

Heliyon

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“…We have already described multicomponent syntheses of chromeno [2,3-b]pyridines [28][29][30][31][32][33][34]. However, there are no reports on a PASE synthesis of hydroxyquinolinone substituted chromeno [2,3-b]pyridines.…”

Section: Introductionmentioning

confidence: 99%

“…, 190 (3), 161(20), 150 (100), 122 (65), 78(16),63 (31), 18(32). HRMS-ESI: [M + H] + , calcd for C 22 H 15 N 6 O 5 443.1104, found 443.1098.…”

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confidence: 99%

Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-b]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism

et al. 2020

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The Pot, Atom, and Step Economy (PASE) approach is based on the Pot economy principle and unites it with the Atom and Step Economy strategies; it ensures high efficiency, simplicity and low waste formation. The PASE approach is widely used in multicomponent chemistry. This approach was adopted for the synthesis of previously unknown hydroxyquinolinone substituted chromeno[2,3-b]pyridines via reaction of salicylaldehydes, malononitrile dimer and hydroxyquinolinone. It was shown that an ethanol-pyridine combination is more beneficial than other inorganic or organic catalysts. Quantum chemical studies showed that chromeno[2,3-b]pyridines has potential for corrosion inhibition. Real time 1H NMR monitoring was used for the investigation of reaction mechanism and 2-((2H-chromen-3-yl)methylene)malononitrile was defined as a key intermediate in the reaction.

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“…In the last few years we also realized multicomponent transformations of salicylaldehydes, 2‐aminoprop‐1‐ene‐1,1,3‐tricarbonitrile (malononitrile dimer) and 3‐phenylisoxazol‐5(4 H )‐one, or 1,3‐cyclohexanediones into 2,4‐diamino‐5‐(5‐oxo‐3‐phenyl‐2,5‐dihydroisoxazol‐4‐yl)‐ or 2,4‐diamino‐5‐(2‐hydroxy‐6‐oxocyclohex‐1‐en‐1‐yl)‐5 H ‐chromeno[2,3‐ b ]pyridine‐3‐carbonitriles.…”

Section: Introductionmentioning

confidence: 99%

Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2,4‐Diamino‐5H‐chromeno[2,3‐b]pyridine Scaffold

et al. 2019

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A new multicomponent reaction is reported: the one‐pot transformation of salicylaldehydes, 2‐aminoprop‐1‐ene‐1,1,3‐tricarbonitrile (malononitrile dimer), and trialkylphosphites results in the efficient formation of (2,4‐diamino‐3‐cyano‐5H‐chromeno[2,3‐b]pyridin‐5‐yl)phosphonates. The scope of this one‐pot reaction was investigated. The isolation of substituted phosphonates is very easy. The optimized reaction conditions and a mechanistic rationale for the complex multicomponent transformation are presented. This facile PASE approach offers a powerful tool for the selective formation of new types of functionalized 5‐P‐substituted 2,4‐diamino‐5H‐chromeno[2,3‐b]pyridine scaffolds containing the phosphonate fragment, which are promising compounds for various biomedical applications, among them the treatment of human inflammatory diseases and cancer therapy.

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Synthesis, structural, spectroscopic and docking studies of new 5C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles

Cited by 32 publications

References 24 publications

Speculative assessment, molecular composition, PDOS, topology exploration (ELF, LOL, RDG), ligand-protein interactions, on 5-bromo-3-nitropyridine-2-carbonitrile

Speculative assessment, molecular composition, PDOS, topology exploration (ELF, LOL, RDG), ligand-protein interactions, on 5-bromo-3-nitropyridine-2-carbonitrile

Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-b]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism

Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2,4‐Diamino‐5H‐chromeno[2,3‐b]pyridine Scaffold

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