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

Autor(en)

Chiara Sulpizio, Alexander Roller, Gerald Giester, Annette Rompel

Abstrakt

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(en)

Institut für Biophysikalische Chemie, Institut für Anorganische Chemie, Institut für Mineralogie und Kristallographie

Journal

Monatshefte für Chemie

Band

147

Seiten

1747-1757

Anzahl der Seiten

11

ISSN

0026-9247

DOI

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

Publikationsdatum

08-2016

Peer-reviewed

Ja

ÖFOS 2012

104017 Physikalische Chemie, 106002 Biochemie, 105113 Kristallographie

Schlagwörter

ASJC Scopus Sachgebiete

Allgemeine Chemie

Link zum Portal

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