Synthesis, structure, and antioxidant activity of methoxy- and hydroxyl-substituted 2'-aminochalcones

Author(s)

Chiara Sulpizio, Alexander Roller, Gerald Giester, Annette Rompel

Abstract

Abstract: Three 2'-aminochalcone derivatives (E)-1-(2-aminophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, (E)-1-(2-aminophenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one, and (E)-1-(2-amino-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one, have been synthesized, characterized, and tested in vitro in order to assess their antioxidant activity. All compounds were characterized on the basis of

¹H NMR,

¹³C NMR, ESI-mass spectrometry, FT-IR, UV/Vis, and elemental analysis. The X-ray crystal structures of (E)-1-(2-aminophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one and (E)-1-(2-amino-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one were successfully determined showing a planar molecule geometry. Studies on the biological properties including test of free radical scavenging ability (DPPH test) and superoxide dismutase mimetic activity were performed. The results indicate that the aminochalcone carrying two hydroxyl functionalities in adjacent meta and para position exhibits a stronger antioxidant activity than the other derivatives. Graphical abstract: [Figure not available: see fulltext.]

Organisation(s)

Department of Biophysical Chemistry, Department of Inorganic Chemistry, Department of Mineralogy and Crystallography

Journal

Monatshefte für Chemie

Volume

147

Pages

1747-1757

No. of pages

11

ISSN

0026-9247

DOI

https://doi.org/10.1007/s00706-016-1812-9

Publication date

08-2016

Peer reviewed

Yes

Austrian Fields of Science 2012

104017 Physical chemistry, 106002 Biochemistry, 105113 Crystallography

Keywords

ASJC Scopus subject areas

General Chemistry

Portal url

https://ucrisportal.univie.ac.at/en/publications/26e5934e-b47e-46c0-8edf-a955fa2256c2