title: Enantioselective synthesis and antioxidant activity of 3,4,5-substituted piperidine derivatives.
abstract: In this study, 3,4,5-trisubstituted piperidines were synthesized enantioselectively, and their antioxidant activity was evaluated. The 3,4,5-trisubstituted piperidines containing TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) and a spatially proximal hydroxy group showed good antioxidant activity. Some of these compounds showed IC50 values in a nanomolar range, comparable to that of TEMPO. Probably the TEMPO generated from the homolysis of the CON bond of 3,4,5-trisubstituted piperidines functions as a radical-scavenging entity, and the hydroxy group of piperidines has a synergistic effect to the antioxidant activity.
authors.affiliation: Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 24252, Republic of Korea.
authors.forename: Jin Ho
authors.initials: JH
authors.lastname: Kim
authors.affiliation: Division of Energy Systems Research, Ajou University, Suwon 16499, Republic of Korea.
authors.forename: Pranab K
authors.initials: PK
authors.lastname: Shyam
authors.affiliation: Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 24252, Republic of Korea.
authors.forename: Mi Jeong
authors.initials: MJ
authors.lastname: Kim
authors.affiliation: Division of Energy Systems Research, Ajou University, Suwon 16499, Republic of Korea.
authors.forename: Hwa-Jung
authors.initials: HJ
authors.lastname: Lee
authors.affiliation: Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 24252, Republic of Korea. Electronic address: leo900516@gmail.com.
authors.forename: Jeong Tae
authors.initials: JT
authors.lastname: Lee
authors.affiliation: Division of Energy Systems Research, Ajou University, Suwon 16499, Republic of Korea; Korea Carbon Capture & Sequestration R&D Center, Deajeon 305-343, Republic of Korea. Electronic address: hyjang2@ajou.ac.kr.
authors.forename: Hye-Young
authors.initials: HY
authors.lastname: Jang
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D010880:Piperidines; C032727:piperidine
keywords: ABTS assay; Antioxidant; Enantioselective reaction; Piperidine; TEMPO