Nguyen Nguyen Tran, Dai Vo Viet, Mechler Adam, Hoa Nguyen Thi, Vo Quan V
The University of Danang - University of Science and Education Danang 550000 Vietnam
Department of Biochemistry and Chemistry, La Trobe University Victoria 3086 Australia.
RSC Adv. 2022 Aug 30;12(38):24579-24588. doi: 10.1039/d2ra04640g.
The heterocyclic γ-lactam ring 2-pyrrolidinone has four carbon atoms and one nitrogen atom. Among the group of derivatives of 2-pyrrolidinones, 1,5-dihydro-2-pyrrol-2-ones, also known as 3-pyrroline-2-ones, play a significant structural role in a variety of bioactive natural compounds. In this study, three-component reactions were used to successfully synthesize six polysubstituted 3-hydroxy-3-pyrroline-2-one derivatives. The antioxidant activity of the compounds was tested by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, identifying 4-ethoxycarbonyl-3-hydroxy-5-(4-methylphenyl)-1-phenyl-3-pyrroline-2-one (4b) as the most promising radical scavenger. Quantum chemistry calculations of the thermodynamics and kinetics of the radical scavenging activity also suggest that 4b is an effective HO˙ radical scavenger, with values of 2.05 × 10 and 1.54 × 10 M s in pentyl ethanoate and water, respectively. On the other hand, 4b could not scavenge hydroperoxyl radicals in either media. The ability of 4b to scavenge hydroxyl radicals in polar and non-polar environments is comparable to that of conventional antioxidants such as melatonin, gallic acid, indole-3-carbinol, ramalin, or Trolox. Thus 4b may be classed as a promising HO˙ radical scavenger in the physiological environment.
杂环γ-内酰胺环2-吡咯烷酮含有四个碳原子和一个氮原子。在2-吡咯烷酮的衍生物中，1,5-二氢-2-吡咯-2-酮，也称为3-吡咯啉-2-酮，在多种生物活性天然化合物中起着重要的结构作用。在本研究中，采用三组分反应成功合成了六种多取代的3-羟基-3-吡咯啉-2-酮衍生物。通过2,2-二苯基-1-苦基肼基（DPPH）测定法测试了这些化合物的抗氧化活性，确定4-乙氧羰基-3-羟基-5-（4-甲基苯基）-1-苯基-3-吡咯啉-2-酮（4b）是最有前景的自由基清除剂。自由基清除活性的热力学和动力学的量子化学计算也表明，4b是一种有效的HO˙自由基清除剂，在乙酸戊酯和水中的值分别为2.05×10和1.54×10 M s。另一方面，4b在两种介质中都不能清除氢过氧自由基。4b在极性和非极性环境中清除羟基自由基的能力与褪黑素、没食子酸、吲哚-3-甲醇、拉马林或曲洛昔康等传统抗氧化剂相当。因此，4b在生理环境中可被归类为一种有前景的HO˙自由基清除剂。
