Synthesis and evaluation of the antioxidant activity of 3-pyrroline-2-ones: experimental and theoretical insights. Issue 38 (30th August 2022)

• Record Type: Journal Article
• Authors: Nguyen, Nguyen Tran; Dai, Vo Viet; Mechler, Adam; Hoa, Nguyen Thi; Vo, Quan V.
• Is Part Of: RSC advances. Volume 12:Issue 38(2022)
• Page Start: 24579
• Page End: 24588
• Publication Date: 2022-08-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2ra04640g
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Derivatives of 3-hydroxy-3-pyrroline-2-one were effectively synthesized via multicomponent reactions and exhibited potential HO˙ radical scavenging activity. Abstract : 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 H -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 k overall values of 2.05 × 10 9 and 1.54 × 10 10 M −1 s −1 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.