@misc{oai:repo.qst.go.jp:00070683,
 author = {Nakanishi, Ikuo and Inami, Keiko and Ohkubo, Kei and Kawashima, Tomonori and Matsumoto, Kenichiro and Fukuhara, Kiyoshi and Mochizuki, Masataka and Fukuzumi, Shunichi and Anzai, Kazunori and Ozawa, Toshihiko and 中西 郁夫 and 川島 知憲 and 松本 謙一郎},
 month = {Feb},
 note = {Since phenolic antioxidants, such as vitamin E (alpha-tocopherol) and catechins, are known to show both antioxidative and prooxidative activities under certain conditions, fine-tuning of such activities is of considerable importance to control oxidative stress induced by reactive oxygen species (ROS) in biological redox systems.  However, very little is known about the structure-activity relationship of the phenolic antioxidants.  In this study, we demonstrate that density functional theory (DFT) calculations of O-H bond dissociation enthalpies and ionization potentials (IP) of phenolic antioxidants are a powerful tool to expect their radical-scavenging activity.  In fact, the logarithms of the second-order rate constants (k) for the scavenging reaction of galvinoxyl radical (GO) as an ROS model by various substituted 6-chromanols, which were synthesized as vitamin E analogues, in deaerated acetonitirile are found to correlate linearly with their IP values calculated by DFT.  Among the derivatives, 8-amino-2,2-dimethylchroman-6-ol having the smallest IP value showed the highest GO-scavenging activity.  Thus, the introduction of substituents, which lower the IP value, to the benzene ring of 6-chromanol results in the enhancement of the antioxidative activity of 6-chromanol derivatives., 第20回日本学術振興会先端研究拠点事業セミナー：International Redox Core Symposium},
 title = {Fine-Tuning of Redox Properties of Substituted 6-Chromanols as Vitamin E Analogues Based on Density Functional Theory Calculations},
 year = {2012}
}