Synthesis, antioxidant and toxicological study of novel pyrimido quinoline derivatives from 4-hydroxy-3-acyl quinolin-2-one

Sankaran, Mathan; Chandraprakash, Kumarasamy; Uvarani, Chokkalingam; Mohan, P. S.

doi:10.1016/j.bmcl.2010.09.018

Cited by 86 publications

(53 citation statements)

References 31 publications

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“…Synthetic quinoline derivatives such as 2-chloroquinoline-3-carboxaldehydes 14 , spiro-substituted 4-hydroxypyranoquinolinones 21 , and pyrimido quinoline derivatives 23 have shown significant antioxidant activity. In this study, quinoline derivatives were synthesized in order to investigate whether the quinoline is a substantial heterocyclic bioisoster of the MLT indole moiety.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Püsküllü

Shirinzadeh

Nenni

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Overproduction of reactive oxygen species results in oxidative stress that can cause fatal damage to vital cell structures. It is known that the use of antioxidants could be beneficial in the prevention or delay of numerous diseases associated with oxidative stress. Melatonin (MLT) is known as a powerful free-radical scavenger and antioxidant. It was found that indole ring of MLT can be employed by bioisosteric replacement by other aromatic rings. Quinoline derivatives constitute an important class of compounds for new drug development. Owing to quinoline and hydrazones appealing physiological properties and are mostly found in numerous biologically active compounds a series of quinoline-2-carbaldehyde hydrazone derivatives were synthesized as bioisosteric analogues of MLT, characterized and in vitro antioxidant activity was investigated by evaluating their reducing effect against oxidation of a redox-sensitive fluorescent probe. Cytotoxicity potential of all compounds was investigated both by lactate dehydrogenase leakage assay and by MTT assay.

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Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Püsküllü

Shirinzadeh

Nenni

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In this study, quinoline compound IMDHPQ alleviated the InTiO NPs mediated oxidative stress with an increase in activities of antioxidant enzymes CAT and GSH-Px, in hepatic samples in dose dependent manner. The above results suggest that 2-imino-4-methyl-1, 2-dihydropyrimido [5, 4C] quinoline-5(6H)-one possesses hepatoprotective property [11,22].…”

Section: Discussionmentioning

confidence: 77%

“…Beneficial effects of the quinoline compound were illustrated in previous study. It may be due to the presence of phenolic hydroxyl, imine unit, and the flavins like structure of the compound [11,22].…”

Section: Discussionmentioning

confidence: 99%

“…Pyrimidoquinoline ring system has structural similarity to naturally occurring flavines. DPPH, FRAP, radical scavenging assays of this compound shown to have antioxidant effect [11]. Hence, the present study was aimed at investigating the hepatoprotective or ameliorative role of the quinoline compound IMDHPQ against InTiO NPs induced hepatotoxicity in experimental albino rats.…”

Section: Introductionmentioning

confidence: 99%

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Indium Titanium Oxide Nanoparticles Induced Hepatic Damage: Hepatoprotective Role of Novel 2-Imino-4-methyl-1, 2-Dihydropyrimido [5, 4C] Quinoline-5(6H)-one

Bheeman¹,

Cheerothsahajan²,

Sathish³

et al. 2014

Advances in Toxicology

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Protective role of 2-imino-4-methyl-1, 2-dihydropyrimido [5, 4C] quinoline-5(6H)-one (IMDHPQ) in indium titanium oxide nanoparticles (InTiO NPs) induced hepatotoxicity was analyzed. InTiO NPs were synthesized and given orally to albino rats to assess their hepatotoxicity. NPs mediated oxidative stress and liver tissue pathology were analyzed. Altered antioxidants (GSH, GPx, and catalase) and, biochemical (SGOT, SGPT, ALP, total protein, and total bilirubin) and histopathological changes were observed due to the oxidative stress caused by InTiO NPs. Varying effects of IMDHPQ on each parameter were observed in the present study. The altered parameters of InTiO NPs exposed rats might be due to the oxidative stress caused by NPs and hepatoprotective or ameliorative efficacy of quinoline compound IMDHPQ on signaling and molecular mechanism needs further study.

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“…Heterocyclic compounds, especially those with nitrogen, are the most important class of compounds in the pharmaceutical and agrochemical industries [1]. Quinoline systems in particular constitute a privileged substructure and are found in numerous biologically active natural products and pharmacologically relevant therapeutic agents [2].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,3-bis(6-methoxyquinolin-2-yl)benzene, C26H20N2O2

Duarte

Gutiérrez

Astudillo

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound, C 26 H 20 N 2 O 2 , was prepared by the reaction of p-anisidine with terephthaldialdehyde and N-vinyl-2-pyrrolidone at room temperature. A mixture of p-anisidine (3 mmol) and isophthalaldehyde (1.5 mmol) in anhydrous CH 3 CN (5 mL) under N 2 , was stirred at room temperature for 1 hour. BiCl 3 (20 mol %) was added. Over a period of 20 min, a solution the N-vinyl-2-pirrolidone (3.1 mmol) in CH 3 CN (5 mL) was added dropwise. The resulting mixture was stirred for 8-10 h. After completion of the reaction as indicated by TLC, the reaction mixture was diluted with (15 mL) and extracted with ethyl acetate (3´10 mL). The organic layer was separated, and dried with Na 2 SO 4 . The organic solvent was removed in vacuo and the resulting product was purified by column chromatography (silica gel, petroleum ether/EtOAc) to afford pure substances, tetrahydroquinoline and 1,3-bis(6-methoxyquinolin-2-yl)benzene. Analysis: Solid crystalline m.p. 224-227°C. 13 C NMR (400 MHz, CDCl 3 ) d: 157.4 (2), 154.6 (2), 144.1 (2), 140 (2), 135.2 (2), 130.9 (2), 128.3 (1), 127.9 (2), 127.6 (2), 126 (1), 122 (2), 119.1 (2), 104.7 (2), 55.2 (2). Experimental detailsH atoms were located in the difference Fourier map, but refined with fixed individual displacement parameters, using a riding model with C-H distances of 0.95 Å (for CH), 0.98 Å (for CH 3 ), with U iso (H) values of 1.2U eq (C) (for CH) and 1.5U eq (C) (for CH 3 ). DiscussionHeterocyclic compounds, especially those with nitrogen, are the most important class of compounds in the pharmaceutical and agrochemical industries [1]. Quinoline systems in particular constitute a privileged substructure and are found in numerous biologically active natural products and pharmacologically relevant therapeutic agents [2]. These organic molecules have attracted attention of both synthetic and medicinal chemists. (12) and 2.96(12)°. In the molecular structure, the most noticeable deviation from planarity are expressed by the torsion angles of the methoxy groups with respect to adjacent quinoline system [C8-O2-C26-C25 = 5.3(3) and C7-

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Synthesis, antioxidant and toxicological study of novel pyrimido quinoline derivatives from 4-hydroxy-3-acyl quinolin-2-one

Cited by 86 publications

References 31 publications

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Indium Titanium Oxide Nanoparticles Induced Hepatic Damage: Hepatoprotective Role of Novel 2-Imino-4-methyl-1, 2-Dihydropyrimido [5, 4C] Quinoline-5(6H)-one

Crystal structure of 1,3-bis(6-methoxyquinolin-2-yl)benzene, C26H20N2O2

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