A Quantum Chemical and Statistical Study of Phenolic Schiff Bases with Antioxidant Activity against DPPH Free Radical

被引：24

作者：

Anouar, El Hassane ^{[1
]}

机构：

[1] Univ Teknol MARA, Atta Ur Rahman Inst Nat Prod Discovery, Puncak Alam Campus Level 9 FF3, Bandar Puncak Alam 42300, Selangor Darul, Malaysia

来源：

ANTIOXIDANTS | 2014年 / 3卷 / 02期

关键词：

Schiff bases; antioxidant activity; DFT; MLR; PCA; HCA; QSAR;

D O I：

10.3390/antiox3020309

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Phenolic Schiff bases are known as powerful antioxidants. To select the electronic, 2D and 3D descriptors responsible for the free radical scavenging ability of a series of 30 phenolic Schiff bases, a set of molecular descriptors were calculated by using B3P86 (Becke's three parameter hybrid functional with Perdew 86 correlation functional) combined with 6-31 + G(d, p) basis set (i.e., at the B3P86/6-31 + G(d, p) level of theory). The chemometric methods, simple and multiple linear regressions (SLR and MLR), principal component analysis (PCA) and hierarchical cluster analysis (HCA) were employed to reduce the dimensionality and to investigate the relationship between the calculated descriptors and the antioxidant activity. The results showed that the antioxidant activity mainly depends on the first and second bond dissociation enthalpies of phenolic hydroxyl groups, the dipole moment and the hydrophobicity descriptors. The antioxidant activity is inversely proportional to the main descriptors. The selected descriptors discriminate the Schiff bases into active and inactive antioxidants.

引用

页码：309 / 322

页数：14

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