Simple C-2-Substituted Quinolines and their Anticancer Activity

Kouznetsov, Vladímir V.; Ruiz, Fernando A. Rojas; Méndez, Leonor Y. Vargas; Gupta, Mahabir P.

doi:10.2174/157018012801319544

Cited by 54 publications

(43 citation statements)

References 21 publications

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“…Quinoline and its derivatives have received considerable attention because of their potential activities such as anticancer (1)(2)(3)(4)(5)(6)(7)(8)(9), anti-inflammatory (10)(11)(12), anti-oxidant, and other biological activities (13)(14)(15)(16)(17).…”

Section: Introductionmentioning

confidence: 99%

Can Functionalization of Quinoline Derivatives Be Exploited to Control Quinolines Cytotoxic Effects?

Hami

Zibaseresht

2017

J Arch Mil Med

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Background: Quinoline and its variety of derivatives have long been studied for their biological activities such as anticancer, antitumor, anti-inflammatory, and antioxidant properties. Objectives: As part of our research, we are interested in the synthesis and development of heterocyclic compounds such as quinoline derivatives and poly-pyridyl materials that might have potential biological activities. Particularly, anti-cancerous and antibacterial properties of such compounds are of our interest. Methods: A previously synthesized mixture of two quinoline derivative isomers (7-methylquinoline and 5-methylquinoline (A + B)) and other four quinoline derivatives (7-methyl-8-nitro-quinoline (C), 7-(β-trans-(N,N-dimethylamino) ethenyl) -8-nitroquinoline (D), 8-nitro-7-quinolinecarbaldehyde (E), and 8-Amino-7-quinolinecarbaldehyde (F)) were selected to evaluate their in vitro cytotoxicity against human epithelial colorectal carcinoma (Caco-2) cultured cells by MTT assay. The IC50 values for the mixture and other compounds were calculated by SigmaPlot 12.0 software.

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Section: Introductionmentioning

confidence: 99%

Can Functionalization of Quinoline Derivatives Be Exploited to Control Quinolines Cytotoxic Effects?

Hami

Zibaseresht

2017

J Arch Mil Med

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“…Searching for structure with potential biological activities we concentrated our attention on quinoline and its congeners which possess diverse and potent pharmacological activities [4] such as antibacterial [5], antifungal [6], antimalarial [7], anticancer [8], antiviral [9], anticonvulsant [10], antiinflammatory [11], antitubercular [12], antidepressant [13], etc. Recent literature is enriched with progressive findings on various and improved method for synthesis of quinoline derivatives [14]. Moreover, this benzofused heteroaromatic ring has been studied and exploited immensely than any other heterocycle for the development of potent pharmacological agents which includes Montelukast (antiasthmatic), Saquinavir (antiviral), Aripiprazole (antipsychotic), etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In‐vitro Antimicrobial Activity of Secondary and Tertiary Amines Containing 2‐Chloro‐6‐methylquinoline Moiety

Kumar

Bawa

Kaushik

et al. 2011

Archiv der Pharmazie

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A number of secondary and tertiary amines bearing 2-chloro-6-methylquinoline were synthesized by nucleophilic substitution reaction of 3-(chloromethyl)-2-chloro-6-methylquinoline with substituted aromatic primary and secondary amines in presence of catalytic amount of triethylamine (TEA) and K(2)CO(3). All the compounds were characterized by combined use of IR, (1)H-NMR, (13)C-NMR, mass spectral data, and microanalyses. The newly synthesized quinolinyl amines were screened in vitro for their antifungal activity against Aspergillus niger MTCC 281, Aspergillus flavus MTCC 277, Monascus purpureus MTCC 369, Penicillium citrinum NCIM 768 and for antibacterial activity strains viz. Escherichia coli NCTC 10418, Staphylococcus aureus NCTC 65710, and Pseudomonas aeruginosa NCTC 10662 by agar diffusion technique. Results of the preliminary screening revealed that some of the compounds mainly those with electron withdrawing groups in the phenyl ring showed promising antifungal activity.

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“…Quinolines have been generally synthesized by wellknown classical methods such as Skraup, Doebner-von Miller, Friedländer's, Ptzinger, Conrad-Limpach, and Combes reactions. 10 Among them, the Friedländer's annulation 11 is still considered as one of the simplest and direct approaches for the synthesis of quinolines. The Friedländer's protocol consists typically of the reactions between aromatic o-aminoketones or aldehydes and another carbonyl compound with an activated α-methylene group.…”

mentioning

confidence: 99%

Optimization of the Reaction Conditions for Synthesis of 3-(Aryloxy)quinoline Derivatives via Friedländer's Cyclization Reaction

Khan¹,

El‐Gamal²,

Oh³

2013

Bulletin of the Korean Chemical Society

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6,7-Dimethoxy-2-methyl-3-(4-nitrophenoxy)quinoline was synthesized by Friedländer's cyclization reaction. Different bases and solvents were tested in order to optimize the reaction conditions. The highest yields were obtained using piperidine in refluxing ethanol. Further reactions were carried out in order to prepare different diarylamide and diarylurea derivatives in moderate to high yields in order to examine their anticancer activities.

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Simple C-2-Substituted Quinolines and their Anticancer Activity

Cited by 54 publications

References 21 publications

Can Functionalization of Quinoline Derivatives Be Exploited to Control Quinolines Cytotoxic Effects?

Can Functionalization of Quinoline Derivatives Be Exploited to Control Quinolines Cytotoxic Effects?

Synthesis and In‐vitro Antimicrobial Activity of Secondary and Tertiary Amines Containing 2‐Chloro‐6‐methylquinoline Moiety

Optimization of the Reaction Conditions for Synthesis of 3-(Aryloxy)quinoline Derivatives via Friedländer's Cyclization Reaction

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