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Anti-oxidation properties of 2-substituted furan derivatives: A mechanistic study
Journal of Luminescence ( IF 3.6 ) Pub Date : 2021-02-01 , DOI: 10.1016/j.jlumin.2020.117725
Naresh Kumar , Anamika Gusain , Jagdeep Kumar , Rajendra Singh , Prasanta Kumar Hota

Abstract 2-(p-phenyl substituted styryl)-furans were synthesized and studied the excited state and anti oxidation properties using absorption, fluorescence, density functional theory and DPPH radical scavenging assay. 2-(p-hydroxy phenyl styryl)-furan (6) exhibits good antioxidant properties with IC50 ~ 40 μM as compared to the amine, chloro, cyano methoxy and nitro substituted styryl compounds (1–5, 7–8) (IC50 > 150 μM). It is shown that furans 1–3 with strong electron withdrawing nitro, cyano and chloro substituent do not show antioxidant properties. The O–H bond dissociation energy (BDE) of p-hydroxy substituted furan compound is comparable to the BDE of vitamin E. The antioxidant activity of furan compound is further reduced with increasing the dipolar nature of the molecule. From the thermodynamic parameters and antioxidant properties, it is shown that there is a correlation of antioxidant properties with the ground state dipole moment, X–H bond dissociation energy (X: O; N) and proton affinity (PA). In presence of the furan compound, the quenching of DPPH radical is occurred predominantly through hydrogen atom transfer mechanism.

中文翻译:

2-取代呋喃衍生物的抗氧化性能:机理研究

摘要 合成了2-(对苯基取代苯乙烯基)-呋喃,并利用吸收、荧光、密度泛函理论和DPPH自由基清除实验研究了其激发态和抗氧化性能。与胺、氯、氰基甲氧基和硝基取代的苯乙烯基化合物 (1–5, 7–8) 相比,2-(p-羟基苯基苯乙烯基)-呋喃 (6) 表现出良好的抗氧化性能,IC50 ~ 40 μM (IC50 > 150 微米)。结果表明,具有强吸电子硝基、氰基和氯取代基的呋喃 1-3 不显示抗氧化性能。对羟基取代的呋喃化合物的 O-H 键解离能 (BDE) 与维生素 E 的 BDE 相当。呋喃化合物的抗氧化活性随着分子偶极性质的增加而进一步降低。从热力学参数和抗氧化性能来看,结果表明,抗氧化性能与基态偶极矩、X-H 键解离能 (X: O; N) 和质子亲和力 (PA) 之间存在相关性。在呋喃化合物的存在下,DPPH自由基的猝灭主要通过氢原子转移机制发生。
更新日期:2021-02-01
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