Design, Synthesis and Biological Evaluation of Ferulic Acid Amides as Selective Matrix Metalloproteinase Inhibitors

Zhi-Hao      Shi; Nian-Guang      Li; Qian-Ping      Shi; Hao-Tang; Yu-Ping      Tang; Wei-Li; Lian-Yin; Jian-Ping      Yang; Jin-Ao      Duan

Abstract

A series of ferulic acid amides with extended P1' groups were synthesized and tested for their inhibitory activities on matrix metalloproteinase (MMP)-1, MMP-2, and MMP-9. Preliminary structure–activity relationship analysis and docking studies indicated that ferulic acid amides with electron-donating groups at the amino phenyl ring showed better inhibitory activities and selectivity than those with electron-withdrawing groups. Compound 3e, which had a hydroxyl group at meta-position of amino phenyl ring, showed considerable inhibitory activities against MMP-2, MMP-9 and best selectivity over MMP-1. The findings of this study would provide information for the exploitation and utilization of ferulic acid as MMP inhibitor for metastatic tumor treatment.

Keywords: Design, ferulic acid, inhibitor, metrix metalloproteinase, structure-activity relationship, tumor.

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