Radical-scavenging activity characterization of a series of synthetic 3-phenylcoumarins

被引：1

作者：

Karadjova, Veronika ^{[2
]}

Vakarelska-Popovska, Maria ^{[1
]}

Velkov, Zhivko ^{[1
]}

机构：

[1] South West Univ NeofitRilski, Dept Chem, Blagoevgrad, Bulgaria

[2] Univ Chem Technol & Met, 8 Kliment Ohridski Str, Sofia 1756, Bulgaria

来源：

COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2021年 / 1202卷

关键词：

3-phenylcoumarins; Radical-scavenging activity; DFT-calculations; Mechanisms of O-H bond dissociations; ANTIOXIDANT ACTIVITY; ELECTRON; ENTHALPIES; PROTON;

D O I：

10.1016/j.comptc.2021.113300

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of synthetic hydroxyl derivatives of 3-phenylcoumarin with already assessed radical-scavenging activity were modeled and treated with quantum-chemistry methods in order to get insight into the structural and energy changes occurring during dissociation of O-H bonds by different mechanisms. The enthalpy changes of each step were calculated and the role of the OH-group positions in the molecules, as well as the influence of the second hydroxyl group on the reactivity were evaluated. The geometry of each intermediate structure was optimized using B3LYP/DFT functional and the standard 6-311++G(d,p) orbital basis set. Solvent effects were accounted for using the SCRF method, via the polarized continuum method.

引用

页数：6

共 24 条

[1] Amorati R, 2017, BIOMIMETICS-BASEL, V2, DOI 10.3390/biomimetics2030009
[2] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR
BECKE, AD
[J]. PHYSICAL REVIEW A, 1988, 38 (06): : 3098 - 3100
[3] Topology delimitedradical-scavengingpropensity of monohydroxycinnamic acids
Borislavov, Lyuben
Velkov, Zhivko
Tadjer, Alia
[J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2020, 120 (22)
[4] ABSOLUTE KINETICS OF HYDROGEN ABSTRACTION FROM ALPHA-TOCOPHEROL BY SEVERAL REACTIVE SPECIES INCLUDING AN ALKYL RADICAL
EVANS, C
SCAIANO, JC
INGOLD, KU
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) : 4589 - 4593
[5] Solvent effects .5. Influence of cavity shape, truncation of electrostatics, and electron correlation ab initio reaction field calculations
Foresman, JB
Keith, TA
Wiberg, KB
Snoonian, J
Frisch, MJ
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (40) : 16098 - 16104
[6] Biological activity of metal ions complexes of chromones, coumarins and flavones
Grazul, Magdalena
Budzisz, Elzbieta
[J]. COORDINATION CHEMISTRY REVIEWS, 2009, 253 (21-22) : 2588 - 2598
[7] A CORRELATION OF REACTION RATES
HAMMOND, GS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (02) : 334 - 338
[8] DFT/B3LYP study of the substituent effect on the reaction enthalpies of the individual steps of single electron transfer-proton transfer and sequential proton loss electron transfer mechanisms of phenols antioxidant action
Klein, Erik
Lukes, Vladimir
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (44) : 12312 - 12320
[9] Density functional theory of electronic structure
Kohn, W
Becke, AD
Parr, RG
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (31) : 12974 - 12980
[10] Coumarins as Antioxidants
Kostova, I.
Bhatia, S.
Grigorov, P.
Balkansky, S.
Parmar, V. S.
Prasad, A. K.
Saso, L.
[J]. CURRENT MEDICINAL CHEMISTRY, 2011, 18 (25) : 3929 - 3951

← 1 2 3 →