Introduction of amino moiety enhances the inhibitory potency of 1-tetralone chalcone derivatives against LPS-stimulated reactive oxygen species production in RAW 264.7 macrophages.
Bioorg Chem
; 87: 495-505, 2019 06.
Article
in En
| MEDLINE
| ID: mdl-30927590
ABSTRACT
The design and synthesis of a series of thirty-two halogenated 1-tetralone or 6-amino-1-tetralone chalcone derivatives was achieved by the Claisen-Schmidt condensation reaction and were evaluated for their inhibitory effects against ROS production in LPS-stimulated RAW 264.7 macrophages. It was observed that the introduction of amino moiety into 1-tetralone skeleton greatly increased the inhibitory potency compared to corresponding 1-tetralone chalcones. Among the synthesized compounds, compound 18 which consists of 6-amino-1-tetralone skeleton together with o-fluorobenzylidene showed the most potent ROS inhibitory effect with IC50 value of 0.25⯱â¯0.13⯵M. SAR analysis revealed that amino moiety at the 6th position of 1-tetralone chalcones have an important role for exerting the greater ROS inhibitory potency in LPS-stimulated RAW 264.7 macrophages than those exhibited by 1-tetralone chalcones alone.
Key words
Full text:
1
Database:
MEDLINE
Main subject:
Reactive Oxygen Species
/
Tetralones
/
Chalcones
/
Macrophages
Limits:
Animals
Language:
En
Journal:
Bioorg Chem
Year:
2019
Type:
Article