A one-pot four-component reaction providing quinoline-based 1,4-dihydropyridines

Ghandi, Mehdi; Zarezadeh, Nahid

doi:10.1007/s13738-015-0596-x

Cited by 7 publications

(11 citation statements)

References 105 publications

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“…Based on the product obtained and earlier reports, [7,21,28] a possible mechanism for the one-pot three-component reaction is depicted in scheme 6. It is presumed that initially, Knoevenagel condensation of tetrazolo[1,5-a]quinoline-4-carbaldehyde and 3-oxo-3-phenylpropanenitrile furnishes the intermediate A.…”

Section: Plausible Mechanismmentioning

confidence: 91%

“…Intrigued by the absence of À NH 2 peak, we referred to the 1 H NMR spectrum of other quinolinyl-1,4-dihydropyridines reported earlier. Mehdi Ghandi et al [7] in 2015 reported a series of quinolinyl-1,4-dihydropyridines, where the À NH 2 proton peak was shown to appear around 6.36-6.43 ppm as a broad singlet. In another report, [27] for 4-aryl-1,4-dihydropyridine À NH 2 proton peak appeared at 7.85 ppm as a broad singlet.…”

Section: Synthesis and Characterization Of Quinolinyl-14-dihydropyrimentioning

confidence: 99%

“…[5] A quinoline-based drug, diarylquinoline TMC207, developed by Johnson and Johnson Pharmaceutical Research and Development, was shown to be a promising drug for multi-drug resistance tuberculosis. [6][7][8] Several quinoline analogs have been known to exhibit a broad range of bioactivities such as antimalarial, [9] antitumor, [10] antituberculosis, [8] anti-inflammatory, [11] and antibacterial. [12] On the other hand, 1,4-dihydropyridines (1,4-DHP) represent a class of nitrogen-containing heterocycles, abundance in many natural products and commercially available drugs [7] such as nicardipine, [13] nifedipine, [14] cilnidipine, [15] nimodipine, [16] and as calcium channel blockers with useful effects on the cardiovascular disorder.…”

Section: Introductionmentioning

confidence: 99%

“…[6][7][8] Several quinoline analogs have been known to exhibit a broad range of bioactivities such as antimalarial, [9] antitumor, [10] antituberculosis, [8] anti-inflammatory, [11] and antibacterial. [12] On the other hand, 1,4-dihydropyridines (1,4-DHP) represent a class of nitrogen-containing heterocycles, abundance in many natural products and commercially available drugs [7] such as nicardipine, [13] nifedipine, [14] cilnidipine, [15] nimodipine, [16] and as calcium channel blockers with useful effects on the cardiovascular disorder. [17] 1,4-Dihydropyridines substituted with bioactive heterocyclic compounds at the 4 th position was demonstrated to possess variant biological activities including, antitubercular, [18] inhibition of multidrug-resistance transporter, [19] and bone anabolic.…”

Section: Introductionmentioning

confidence: 99%

“…Further, simple structural variations to the reactant components would lead to diverse organic molecules. [4,7,21] Recently, Sangani et al and Isaivani Dhinakaran et al adopted a one-pot multi-component process for the synthesis of quinolinyl-1,4-dihydropyridines and polysubstituted tetrahydropyridines respectively. [4,21] In the present study, highly substituted quinolinyl-1,4-dihydropyridines were obtained by reacting tetrazole[1,5-a] quinoline-4-carbaldehyde, 3-oxo-3-phenylpropanenitrile, and β-enamines in one-pot (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Multi‐Component Approach for Synthesis of Quinolinyl‐1,4‐dihydropyridines, Evaluation of Cytotoxicity against MCF7 and Molecular Docking Studies

et al. 2020

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Tetrazolo[1,5‐a]quinoline‐4‐carbaldehyde, 3‐oxo‐3‐phenylpropanenitrile, and β‐enamine were reacted in one‐pot to obtain highly functionalized quinolinyl‐1,4‐dihydropyridines. In addition to spectroscopic characterization, the structure of one of the compound is confirmed by single‐crystal X‐ray diffraction. Among all compounds evaluated for cytotoxic effect against MCF7, three quinolinyl‐1,4‐dihydropyridines (SKS13, 19, and 20) were found to be most active with half inhibition concentrations value of 7.87–9.55 μM. Molecular docking of the active molecules to various breast cancer targets revealed effective compounds have multiple receptor targeting potential in breast cancer. Our results corroborate quinolinyl‐1,4‐dihydropyridines as a valuable scaffold to develop anticancer drugs.

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Section: Plausible Mechanismmentioning

confidence: 91%

Section: Synthesis and Characterization Of Quinolinyl-14-dihydropyrimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Multi‐Component Approach for Synthesis of Quinolinyl‐1,4‐dihydropyridines, Evaluation of Cytotoxicity against MCF7 and Molecular Docking Studies

et al. 2020

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Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

et al. 2022

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Quinoline is a significant scaffold among heterocyclic compounds and can be used as a key building block for the development of novel medications. Quinoline and its derivatives are recognised as biologically active substances with a number of pharmacological properties. Nowadays, quinolinebased heterocycle scaffolds have achieved a prominent position in medicinal chemistry due to their significant pharmaco-logical and biological properties. The discovery and creation of cutting-edge medications to treat a variety of diseases is an example of the usefulness of these compounds. The current study outlines the range of methods available to create different quinolone-based heterocycle scaffolds and their advantageous therapeutic applications using the literature that has been published up to 2022.

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Efficient Synthesis of Highly Substituted N‐Arylamino quinolone‐based Pyrrolo[3,4‐b]pyridines and Pyrazolone‐based Pyrrolo[3,4‐b]pyridines Through a One‐Pot Three‐Component Reaction

Alizadeh,

Moterassed,

Rostampoor

2023

ChemistrySelect

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In this research, a simple and efficient strategy for the straightforward synthesis of multisubstituted N-arylamino quinolone-based pyrrolo [3,4-b]pyridine derivatives and pyrazolone-based pyrrolo [3,4-b]pyridine derivatives is presented by a sequential three-component reaction of α-aminomaleimides, 2chloroquinoline-3-carbaldehyde/5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and malononitrile/ethyl 2-cyanoacetate as readily available starting materials in EtOH at room temperature. The merit of this sequential Michael addition/ intramolecular cyclization is highlighted by its high energy conserving (short reaction times at room temperature) excellent yields, metal-free catalyst, and green and mild conditions in a one-pot reaction. With this synthesis, group-assistantpurification (GAP) chemistry can be simplified by eliminating chromatography and recrystallization, and the pure products can be obtained by washing the crude products with 95 % ethanol. Their structures were characterized by spectroscopic data IR, MS, 1 H, and 13 C NMR analysis.

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A one-pot four-component reaction providing quinoline-based 1,4-dihydropyridines

Cited by 7 publications

References 105 publications

Multi‐Component Approach for Synthesis of Quinolinyl‐1,4‐dihydropyridines, Evaluation of Cytotoxicity against MCF7 and Molecular Docking Studies

Multi‐Component Approach for Synthesis of Quinolinyl‐1,4‐dihydropyridines, Evaluation of Cytotoxicity against MCF7 and Molecular Docking Studies

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

Efficient Synthesis of Highly Substituted N‐Arylamino quinolone‐based Pyrrolo[3,4‐b]pyridines and Pyrazolone‐based Pyrrolo[3,4‐b]pyridines Through a One‐Pot Three‐Component Reaction

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