In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives-SAR, QSAR and DFT Studies
In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives-SAR, QSAR and DFT Studies
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DOI：
10.3390/ijms12052822
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发表时间：
2011-05-01
影响因子：
5.6
通讯作者：
Solujic, Slavica
中科院分区：
文献类型：
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作者：
Mladenovic, Milan;Mihailovic, Mirjana;Solujic, Slavica
对合成的15个4-羟基香豆素衍生物进行了体外抗氧化活性评价，包括总抗氧化能力、DPPH自由基、羟自由基、脂质过氧化物清除能力和螯合能力。在自由基清除过程中检测到最高活性，其中2b、6 b、2c和4c被注意到为最活跃。通过定量构效关系（QSAR）研究进一步量化了抗氧化活性。为此，使用参数化方法6（PM 6）半经验和密度泛函理论（DFT）B3 LYP方法优化结构。通过对香豆素4-OH的键解离谱、自然键轨道（NBO）中氧原子的杂化、氢原子的酸性以及各种分子描述符的计算，将其与生物活性进行了关联，设计了20个新的抗氧化剂结构，利用最有利的结构基序，大大提高了体外预测活性。
The series of fifteen synthesized 4-hydroxycoumarin derivatives was subjected to antioxidant activity evaluation in vitro, through total antioxidant capacity, 1,1-diphenyl-2-picryl-hydrazyl (DPPH), hydroxyl radical, lipid peroxide scavenging and chelating activity. The highest activity was detected during the radicals scavenging, with 2b, 6b, 2c, and 4c noticed as the most active. The antioxidant activity was further quantified by the quantitative structure-activity relationships (QSAR) studies. For this purpose, the structures were optimized using Paramethric Method 6 (PM6) semi-empirical and Density Functional Theory (DFT) B3LYP methods. Bond dissociation enthalpies of coumarin 4-OH, Natural Bond Orbital (NBO) gained hybridization of the oxygen, acidity of the hydrogen atom and various molecular descriptors obtained, were correlated with biological activity, after which we designed 20 new antioxidant structures, using the most favorable structural motifs, with much improved predicted activity in vitro.