Birsa Mihail Lucian, Sarbu Laura Gabriela
Department of Chemistry, Alexandru Ioan Cuza University of Iasi, 11 Carol I Blvd., 700506 Iasi, Romania.
Int J Mol Sci. 2024 Dec 21;25(24):13698. doi: 10.3390/ijms252413698.
The antioxidant properties of some 3-dithiocarbamic flavanones were investigated. Based on a previous study, we selected three frameworks that proved to be the most active ones. By varying the nature of the substituent at the para-position of flavanone ring , a structure-activity relationship study on radical scavenging activities was performed. The influence of these substituents (H, F, Cl, Br and I) was evaluated in relation to DPPH, ABTS and FRAP. The results indicated that the presence of the halogen substituent induced better antioxidant properties than ascorbic acid and BHT. The radical scavenging activities were found to decrease in the following order: F > Cl > Br > I > H. This is correlated with the decrease in electronegativity and withdrawing inductive effect of these substituents, which make the C(2)-H bond of the benzopyran ring prone to hydrogen radical transfer.
研究了一些3-二硫代氨基甲酰基黄烷酮的抗氧化性能。基于先前的一项研究，我们选择了三个被证明是最具活性的骨架。通过改变黄烷酮环对位取代基的性质，对自由基清除活性进行了构效关系研究。评估了这些取代基（H、F、Cl、Br和I）对DPPH、ABTS和FRAP的影响。结果表明，卤素取代基的存在诱导出比抗坏血酸和BHT更好的抗氧化性能。发现自由基清除活性按以下顺序降低：F＞Cl＞Br＞I＞H。这与这些取代基的电负性降低和吸电子诱导效应相关，这使得苯并吡喃环的C(2)-H键易于发生氢自由基转移。
