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首页> 美国卫生研究院文献>Molecules >New Phenolic Derivatives of Thiazolidine-24-dione with Antioxidant and Antiradical Properties: Synthesis Characterization In Vitro Evaluation and Quantum Studies
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New Phenolic Derivatives of Thiazolidine-24-dione with Antioxidant and Antiradical Properties: Synthesis Characterization In Vitro Evaluation and Quantum Studies

机译：具有抗氧化和抗自由基性能的新型噻唑烷-24-二酮酚类衍生物：合成表征体外评估和量子研究

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Oxidative stress has been incriminated in the physiopathology of many diseases, such as diabetes, cancer, atherosclerosis, and cardiovascular and neurodegenerative diseases. There is a great interest in developing new antioxidants that could be useful for preventing and treating conditions for which oxidative stress is suggested as the root cause. The thiazolidine-2,4-dione derivatives have been reported to possess various pharmacological activities and the phenol moiety is known as a pharmacophore in many naturally occurring and synthetic antioxidants. Twelve new phenolic derivatives of thiazolidine-2,4-dione were synthesized and physicochemically characterized. The antioxidant capacity of the synthesized compounds was assessed through several in vitro antiradical, electron transfer, and Fe2+ chelation assays. The top polyphenolic compounds >5f and >5l acted as potent antiradical and electron donors, with activity comparable to the reference antioxidants used. The ferrous ion chelation capacity of the newly synthesized compounds was modest. Several quantum descriptors were calculated in order to evaluate their influence on the antioxidant and antiradical properties of the compounds and the chemoselectivity of the radical generation reactions has been evaluated. The correlation with the energetic level of the frontier orbitals partially explained the antioxidant activity, whereas a better correlation was found while evaluating the O–H bond dissociation energy of the phenolic groups.
机译：在许多疾病的生理病理学中已将氧化应激归罪，例如糖尿病，癌症，动脉粥样硬化以及心血管和神经退行性疾病。人们对开发新的抗氧化剂很有兴趣，这些抗氧化剂可用于预防和治疗氧化应激被认为是根本原因的疾病。据报道，噻唑烷-2，4-二酮衍生物具有多种药理活性，并且在许多天然和合成的抗氧化剂中，酚部分被称为药效团。合成并物理化学表征了十二种新的噻唑烷-2,4-二酮酚类衍生物。通过几种体外抗自由基，电子转移和Fe 2 + 螯合试验评估了合成化合物的抗氧化能力。顶部的多酚化合物> 5f 和> 5l 充当了强大的自由基和电子给体，其活性可与所用的参考抗氧化剂相媲美。新合成的化合物的亚铁离子螯合能力中等。计算了几个量子描述符，以评估它们对化合物的抗氧化剂和抗自由基性能的影响，并评估了自由基生成反应的化学选择性。与边界轨道的高能级的相关性部分地解释了抗氧化活性，而在评估酚基的O-H键离解能时发现了更好的相关性。

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