title: Synthesis, structure, and antioxidant activity of methoxy- and hydroxyl-substituted 2'-aminochalcones.
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 of1H 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 adjacentmetaandparaposition exhibits a stronger antioxidant activity than the other derivatives.
authors.affiliation: Fakultät für Chemie, Institut für Biophysikalische Chemie, Universität Wien, Althanstraße 14, 1090 Vienna, Austria.
authors.forename: Chiara
authors.initials: C
authors.lastname: Sulpizio
authors.affiliation: Fakultät für Chemie, Institut für Anorganische Chemie, Universität Wien, Währinger Straße 42, 1090 Vienna, Austria.
authors.forename: Alexander
authors.initials: A
authors.lastname: Roller
authors.affiliation: Fakultät für Geowissenschaften, Geographie und Astronomie, Institut für Mineralogie und Kristallographie, Universität Wien, Althanstraße 14, 1090 Vienna, Austria.
authors.forename: Gerald
authors.initials: G
authors.lastname: Giester
authors.affiliation: Fakultät für Chemie, Institut für Biophysikalische Chemie, Universität Wien, Althanstraße 14, 1090 Vienna, Austria.
authors.forename: Annette
authors.identifier: 0000-0002-5919-0553
authors.initials: A
authors.lastname: Rompel
keywords: Antioxidant activity; Claisen condensation; Structure activity relationship; X-ray structure determination