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快速、环保合成新型多功能吡咯衍生物及其抗氧化性能评价。

Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property.

机构信息

Department of Chemistry, University of Calcutta, 92, A. P. C. Road, Kolkata 700 009, India.

Department of Chemistry, University of Calcutta, 92, A. P. C. Road, Kolkata 700 009, India.

出版信息

Bioorg Chem. 2020 May;98:103734. doi: 10.1016/j.bioorg.2020.103734. Epub 2020 Mar 7.

Abstract

Diminution of oxidative stress-mediated diseases is an essential pharmaceutical objective in modern biomedical research. The present work stresses upon the efficient and eco-friendly synthesis of an array of novel diversely functionalized pyrrole derivatives which are found to be antioxidants with reactive oxygen species (ROS) shielding competency against the deleterious consequence of oxidative stress. The results of the investigation displayed the effect of structural modification of the pyrrole derivatives on their respective antioxidant properties to various ROS. Noteworthy, the pyrrole moiety bearing 4-hydroxycoumarin or 2-hydroxy-1,4-naphthoquinone as substituent showed outstanding defensive potency towards OH and O while, nitrogen atom linked with aliphatic side-chain in the pyrrole scaffold made a strong affirmative impression in DPPH scavenging assay. More interestingly, an influencing reducing power was observed in pyrrole derivatives carrying cyclohexane 1,3-dione as one of the substituents. To have a comprehensive acuteness into the antioxidant capacity of the synthesized pyrrole derivatives against Trolox as a standard antioxidant, a crucial approach was taken into account by calculating TEAC (Trolox Equivalent Antioxidant Capacity) in case of OH and DPPH scavenging activity.

摘要

减轻氧化应激介导的疾病是现代生物医学研究中的一个重要药物目标。本工作强调了一系列新型多样化功能化吡咯衍生物的有效和环保合成,这些衍生物被发现是具有抗氧化活性的物质,具有活性氧 (ROS) 屏蔽能力,可以防止氧化应激的有害后果。研究结果显示了吡咯衍生物的结构修饰对其各自对抗各种 ROS 的抗氧化性能的影响。值得注意的是,带有 4-羟基香豆素或 2-羟基-1,4-萘醌作为取代基的吡咯部分对 OH 和 O 显示出出色的防御能力,而在吡咯骨架中与脂肪侧链相连的氮原子在 DPPH 清除测定中产生了强烈的积极印象。更有趣的是,在带有环己烷 1,3-二酮作为取代基之一的吡咯衍生物中观察到了影响还原能力。为了全面了解合成的吡咯衍生物对 Trolox(一种标准抗氧化剂)的抗氧化能力,我们考虑了一种关键方法,即通过计算 TEAC(Trolox 等效抗氧化能力)来评估 OH 和 DPPH 清除活性。

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