Theoretical elucidation on structure-antioxidant activity relationships for indolinonic hydroxylamines.
Indolinonic hydroxylamines (IH), representing a new type of antioxidants, are comparative to alpha-tocopherol to protect lipids from oxidation. To elucidate the structure-activity relationship for IH, B3LYP/6-31G(d, p) method was employed to calculate the O-H bond dissociation enthalpy (BDE), a theoretical parameter to characterize the free radical scavenging activity. By constructing several model molecules, it was revealed that hydroxylamine was the key structural factor for this type of antioxidants, and substituents had little effect on the O-H BDE. If the =NR of IH was substituted by =O, its activity got lower.
Zhang
Hong-Yu
HY
Laboratory for Computational Biology, Shandong Provincial Research Center for Bioinformatic Engineering and Technique, Shandong University of Technology, Zibo 255091, PR China. zhang630@mail.zbu.net.cn
Wang
Lan-Fen
LF
D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006898:Hydroxylamines / Q000737:chemistry* / Q000494:pharmacology*; D007211:Indoles / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000975:Antioxidants; D016166:Free Radical Scavengers; D006898:Hydroxylamines; D007211:Indoles; C057812:indoline