Antioxidant and antiproliferative activities of hydroxyl-substituted Schiff bases

Cheng, Lü; Tang, Jiang‐Jiang; Luo, Hui; Jin, Xiaoling; Dai, Fang; Yang, Jie; Qian, Yi-Ping; Li, Xiu-Zhuang; Zhou, Bo

doi:10.1016/j.bmcl.2010.03.039

Cited by 122 publications

(53 citation statements)

References 33 publications

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“…Schiff and Mannich bases with various functional groups have also been shown to possess anti-inflammatory and antimicrobial activities [34][35][36] . In addition, there are a number of studies reporting good anticancer activities of Schiff and Mannich bases [37][38][39] . All of the compounds synthesized in this study showed antioxidant activity in both antioxidant tests at various extends (Figures 1-3).…”

Section: Biological Activitiesmentioning

confidence: 99%

Synthesis of new 1,2,4-triazole compounds containing Schiff and Mannich bases (morpholine) with antioxidant and antimicrobial activities

Ünver

Deniz

Çelik

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Compound 2 was synthesized by reacting CS 2 /KOH with compound 1. The treatment of compound 2 with hydrazine hydrate produced compound 3. Then, compound 3 was converted to Schiff bases (4a-d) by the handling with several aromatic aldehydes. The treatment of triazole compounds 4a-d containing Schiff base with morpholine gave compounds 5a-d. All compounds were tested for their antioxidant and antimicrobial activities. The antioxidant test results of DPPH radical scavenging and ferric reducing/antioxidant power methods showed good antioxidant activity. The triazole-thiol (3) was the most active, and the effect of the substituent type of the thiophene ring on the activity was same for both Schiff bases (4a-d) and Mannich bases (5a-d). Among the newly synthesized triazole derivatives, the Schiff base 4d and the Mannich base 5d carrying nitro substituent on the thiophene ring showed promising antibacterial and antifungal activity, with lower MIC values than the standard antibacterial ampicillin.

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Section: Biological Activitiesmentioning

confidence: 99%

Synthesis of new 1,2,4-triazole compounds containing Schiff and Mannich bases (morpholine) with antioxidant and antimicrobial activities

Ünver

Deniz

Çelik

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…IRA’s bearing different functional groups at different positions of the aromatic rings have been synthesized by several groups (e.g. [23–26]). In spite of this and the fairly easy synthesis of most compounds [27], data on the biological activity of these substances is limited, especially regarding their anticarcinogenic properties.…”

Section: Introductionmentioning

confidence: 99%

Growth-Inhibiting Activity of Resveratrol Imine Analogs on Tumor Cells In Vitro

Wang¹,

Willenberg²,

Krohn

et al. 2017

PLoS ONE

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Although resveratrol exerts manifold antitumorigenic effects in vitro, its efficacy against malignancies in vivo seems limited. This has been increasingly recognized in recent years and has prompted scientists to search for structurally related compounds with more promising anticarcinogenic and/or pharmacokinetic properties. A class of structurally modified resveratrol derivatives, so-called resveratrol imine analogs (IRA’s), might meet these requirements. Therefore, the biological activity of five of these compounds was examined and compared to that of resveratrol. Firstly, the antiproliferative potency of all five IRA’s was investigated using the p53 wildtype-carrying colorectal carcinoma cell line HCT-116wt. Then, using the former and a panel of various other tumor cell lines (including the p53 knockout variant HCT-116p53-/-), the growth-inhibiting and cell cycle-disturbing effects of the most potent IRA (IRA 5, 2-[[(2-hydroxyphenyl)methylene]amino]-phenol) were studied as was its influence on cyclooxygenase-2 expression and activity. Finally, rat liver microsomes were used to determine the metabolic stability of that compound. IRA 5 was clearly the most potent compound in HCT-116wt cells, with an unusually high IC50-value of 0.6 μM. However, in the other five cell lines used, the antiproliferative activity was mostly similar to resveratrol and the effects on the cell cycle were heterogeneous. Although all cell lines were affected by treatment with IRA 5, cells expressing functional p53 seemed to react more sensitively, suggesting that this protein plays a modulating role in the induction of IRA 5-mediated biological effects. Lastly, IRA 5 led to contradictory effects on cyclooxygenase-2 expression and activity and was less glucuronidated than resveratrol. As IRA 5 is approximately 50 times more toxic towards HCT-116wt cells, exerts different effects on the cyclooxygenase-2 and is metabolized to a lesser extent, it shows certain advantages over resveratrol and could therefore serve as basis for additional chemical modifications, potentially yielding compounds with more favorable biological and pharmacokinetic features.

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“…[4][5][6][7][8][9] The biological activity of these compounds results in a wide variety of effects, including antidepressant, analgesic, anti-inflammatory, antiplatelet, antimalarial, antimicrobial, antimycobacterial, antitumor and antioxidant. [9][10][11] However, the antifungal activity of hydrazones is known only from reports on acylhydrazones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Diaryl Hydrazones From 2,4-Dinitrophenylhydrazine

Ortíz

Nelson

Kesternich

et al. 2016

J. Chil. Chem. Soc.

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A new series of diarylhydrazones derived from 2,4-dinitrophenylhydrazine were synthesized via condensation with aromatic aldehydes whose structures have been determined by mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectra. Yields were 50-99%. All compounds were screened in vitro for their antifungal activity. Preliminary results indicated that compounds 3g and 3h exhibited promising antifungal potency. Understanding of the structure of these compounds establishes a preliminary structure-activity relationship to form the basis of further investigation.

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Antioxidant and antiproliferative activities of hydroxyl-substituted Schiff bases

Cited by 122 publications

References 33 publications

Synthesis of new 1,2,4-triazole compounds containing Schiff and Mannich bases (morpholine) with antioxidant and antimicrobial activities

Synthesis of new 1,2,4-triazole compounds containing Schiff and Mannich bases (morpholine) with antioxidant and antimicrobial activities

Growth-Inhibiting Activity of Resveratrol Imine Analogs on Tumor Cells In Vitro

Synthesis and Antifungal Activity of Diaryl Hydrazones From 2,4-Dinitrophenylhydrazine

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