Design and Synthesis of Fluorinated and/or Hydroxylated 2‐Arylidene‐1‐indanone Derivatives as an Inhibitor of LPS‐stimulated ROS Production in RAW 264.7 Macrophages with Structure–Activity Relationship Study

Abstract

A new series of thirty-two fluorinated and/or hydroxylated 2-arylidene-1-indanone derivatives were systematically designed, synthesized, and evaluated for their inhibitory activity against LPS-stimulated ROS production in RAW 264.7 macrophages. 5/6-Fluoro-1-indanone or 4-, 5-, 6-, or 7-hydroxyindanone moiety along with ortho-, meta-, or para-hydroxyphenyl, furanyl or thiophenyl moiety was prepared and evaluated. Among the synthesized compounds, compound 11 possessing 6-hydroxy-1-indanone moiety along with 5-chlorothiophenyl moiety was found to have the most potent inhibitory effect on the production of ROS in LPS-stimulated RAW 264.7 macrophages with an IC50 value of 3.29 μM.