Antiproliferative and antioxidative effects of novel hydrazone derivatives bearing coumarin and chromene moiety

被引：0
作者：
Violina T. Angelova
Nikolay G. Vassilev
Boryana Nikolova-Mladenova
Jasmina Vitas
Radomir Malbaša
Georgi Momekov
Mirjana Djukic
Luciano Saso
机构：
[1] Medical University,Department of Chemistry, Faculty of Pharmacy
[2] Bulgarian Academy of Sciences,Laboratory of Nuclear Magnetic Resonance, Institute of Organic Chemistry with Centre of Phytochemistry
[3] University of Novi Sad,Faculty of Technology, Department of Applied and Engineering Chemistry
[4] Medical University,Department of Pharmacology, Pharmacotherapy and Toxicology, Faculty of Pharmacy
[5] University of Belgrade,Department of Toxicology, Faculty of Pharmacy
[6] Sapienza University of Rome,Department of Physiology and Pharmacology “Vittorio Erspamer”
来源：
Medicinal Chemistry Research | 2016年 / 25卷
关键词：
Antioxidant activity; Antiproliferative agents; 2; -Chromene; Coumarins; Hydrazides/Hydrazones; MTT-assay;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
[inline-graphic not available: see fulltext] A series of new hybrid molecules with a hydrazone fragment were synthesized and characterized by Fourier transform-infrared spectroscopy, nuclear magnetic resonance, mass spectrometry, and elemental analysis. The nuclear magnetic resonance spectra of the hydrazones 4a–c showed exchange of syn and antiperiplanar conformers around the amide bond, the more stable being the antiperiplanar one. The nuclear Overhauser effect spectroscopy (NOESY) spectra confirm E configuration around C=N bond. The tested compounds exhibited concentration-dependent cytotoxic effects against human tumor cell lines in a micromolar range (MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) tetrazolium reduction assay). Hydrazone 4a proved to be the most potent antiproliferative agent of the series. Within the antioxidant screening 8b exhibited the highest radical scavenging activity (% RSA max) and the largest rate constant for the reaction with 2,2-diphenyl-1-picrylhydrazyl.
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页码：2082 / 2092
页数：10
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  • [1] Abdel-Aziz HA(2012)Synthesis and pharmacophoric model building of novel substituted nicotinic acid hydrazones with potential antiproliferative activity Arch Pharm Res 35 1543-1552
  • [2] Aboul-Fadl T(2013)Synthesis and anticancer potential of certain novel 2-oxo- Eur J Med Chem 70 358-363
  • [3] Abdul-Rahman MAl-Obaid(2013)-(2-oxoindolin-3-ylidene)-2 Eur J Med Chem 70 358-363
  • [4] Ghazzali M(2015)-chromene-3-carbohydrazides Bull Korean Chem Soc 36 682-691
  • [5] Al-Dhfyan A(2014)Synthesis, crystal structure, and biological activity of cis/trans amide rotomers of (Z)-N-(2-oxoindolin-3-ylidene)formohydrazide Int J Advanced Chem 2 85-103
  • [6] Contini A(2013)Quantum-chemical studies to approach the antioxidant mechanism of nonphenolic hydrazone Schiff base analogs: synthesis, molecular structure, Hirshfeld and density functional theory analyses Eur J Med Chem 59 15-22
  • [7] Abdel-Aziz HA(2003)Pharmacologically potentials of hydrazonone containing compounds: a promising scaffold British J Pharmacology 138 819-830
  • [8] Elsaman T(1995)2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents Lebensm Wiss Technol 28 25-30
  • [9] Al-Dhfyan A(2003)Identification of the di-pyridyl ketone isonicotinoyl hydrazone (PKIH) analogues as potent iron chelators and anti-tumor agents Clin Cancer Res 9 402-414
  • [10] Attia MI(2003)Use of a free radical method to evaluate antioxidant activity Am J Hematology 73 200-210
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