A DFT study on the deprotonation antioxidant mechanistic step of ortho-substituted phenolic cation radicals

Vafiadis, Anastasios P.; Bakalbassis, Evangelos G.

doi:10.1016/j.chemphys.2005.05.015

Cited by 56 publications

(40 citation statements)

References 35 publications

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“…Fundamental research shows that the function of antioxidants is to intercept and react with free radicals at a rate faster than other substrates, including lipids, fats, and proteins. Among these competitive reactions, there are three generally accepted mechanisms of polyphenolic antioxidant action, specifically, hydrogen atom transfer (HAT), single-electron transfer-proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) [7][8][9]. However, even based on these mechanisms, the interactions of the molecular structures of our target compounds and the details of the factors that influence their antioxidant activities still remain quite challenging to describe.…”

Section: Introductionmentioning

confidence: 98%

Structure, electronic properties, and radical scavenging mechanisms of daidzein, genistein, formononetin, and biochanin A: A density functional study

Zhang

Peng

et al. 2010

Journal of Molecular Structure: THEOCHEM

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Section: Introductionmentioning

confidence: 98%

Structure, electronic properties, and radical scavenging mechanisms of daidzein, genistein, formononetin, and biochanin A: A density functional study

Zhang

Peng

et al. 2010

Journal of Molecular Structure: THEOCHEM

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“…From a theoretical point of view, it is possible to find few works devoted to the gas-phase O-H and S-H bond dissociation enthalpies of cyanophenols, cyanothiophenols, and Struct Chem (2007) 18: [15][16][17][18][19][20][21][22][23] [16,17]. Very recently, Matos et al [11] used the MP2, BP, and B3LYP methods together with double-ζ basis set to estimate the standard molar enthalpies of formation in the gas-phase of the three cyanophenol isomers 10 , and used the B3LYP method with different basis sets to estimate the enthalpy of formation of anthranil and 1,2-benzisoxazole.…”

Section: Introductionmentioning

confidence: 99%

The thermodynamics of the isomerization of cyanophenol and cyanothiophenol compounds

2006

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The relative thermodynamics of 12 isomers of both cyanophenol and cyanothiophenol have been computed by DFT and composite approaches. It is shown that these methodologies are capable of correctly reproducing the energetics of the three cyanophenols, anthranil, and phenylisocyanate but have a fair behavior when dealing with benzoxazole and benzothiazole compounds. The estimated values for the latter two species are always less positive than the experimental results, indicating that the theoretical approaches predict a much too stable compound.

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“…[9]. Antioxidant activity is chiefly based on three molecular mechanisms: (a) hydrogen atom transfer (HAT), (b) singleelectron transfer followed by proton transfer (SET-PT), and (c) sequential proton loss electron transfer (SPLET) [10][11][12]. However, under certain circumstances (such as acute or chronic alcohol exposure, or improper diet, etc.…”

Section: Introductionmentioning

confidence: 99%

Development of multiple QSAR models for consensus predictions and unified mechanistic interpretations of the free-radical scavenging activities of chromone derivatives

2011

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Antioxidants are important defenders of the human body against nocive free radicals, which are the causative agents of most life-threatening diseases. The immense biomedicinal utility of antioxidants necessitates the development and design of new synthetic antioxidant molecules. The present report deals with the modeling of a series of chromone derivatives, which was done to provide detailed insight into the main structural fragments that impart antioxidant activity to these molecules. Four different quantitative structure-property relationship (QSAR) techniques, namely 3D pharmacophore mapping, comparative molecular similarity indices analysis (CoMSIA 3D-QSAR), hologram QSAR (HQSAR), and group-based QSAR (G-QSAR) techniques, were employed to obtain statistically significant models with encouraging external predictive potentials. Moreover, the visual contribution maps obtained for the different models signify the importance of different structural features in specific regions of the chromone nucleus. Additionally, the G-QSAR models determine the composite influence of pairs of substituent fragments on the overall antioxidant activity profiles of the molecules. Multiple models with different strategies for assessing structure-activity relationships were applied to reach a unified conclusion regarding the antioxidant mechanism and to provide consensus predictions, which are more reliable than values derived from a single model. The structural information obtained from the various QSAR models developed in the present work can thus be effectively utilized to design and predict the activities of new molecules belonging to the class of chromone derivatives.

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A DFT study on the deprotonation antioxidant mechanistic step of ortho-substituted phenolic cation radicals

Cited by 56 publications

References 35 publications

Structure, electronic properties, and radical scavenging mechanisms of daidzein, genistein, formononetin, and biochanin A: A density functional study

Structure, electronic properties, and radical scavenging mechanisms of daidzein, genistein, formononetin, and biochanin A: A density functional study

The thermodynamics of the isomerization of cyanophenol and cyanothiophenol compounds

Development of multiple QSAR models for consensus predictions and unified mechanistic interpretations of the free-radical scavenging activities of chromone derivatives

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