Enantioselective synthesis and antioxidant activity of 3, 4, 5-substituted piperidine derivatives. Issue 13 (1st July 2016)

• Record Type: Journal Article
• Authors: Kim, Jin Ho; Shyam, Pranab K.; Kim, Mi Jeong; Lee, Hwa-Jung; Lee, Jeong Tae; Jang, Hye-Young
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 13(2016)
• Page Start: 3119
• Page End: 3121
• Publication Date: 2016-07-01
• Subjects: Piperidine -- TEMPO -- Enantioselective reaction -- Antioxidant -- ABTS assay; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2016.04.092
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: 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.