Design, synthesis and biological evaluation of ferulic Acid amides as selective matrix metalloproteinase inhibitors.

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.

• Authors: Zhi-Hao Shi, Nian-Guang Li, Qian-Ping Shi, Hao- Tang, Yu-Ping Tang, Wei- Li, Lian- Yin, Jian-Ping Yang, Jin-Ao Duan
• Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) (Med Chem) Vol. 9 Issue 7 Pg. 947-54 (Nov 2013) ISSN: 1875-6638 [Electronic] Netherlands
• PMID: 23061601 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Amides
• Coumaric Acids
• Matrix Metalloproteinase Inhibitors
• ferulic acid
• Matrix Metalloproteinases

Topics

• Amides (chemical synthesis, chemistry, pharmacology)
• Binding Sites
• Coumaric Acids (chemical synthesis, chemistry, pharmacology)
• Enzyme Activation (drug effects)
• Inhibitory Concentration 50
• Matrix Metalloproteinase Inhibitors (chemical synthesis, chemistry, pharmacology)
• Matrix Metalloproteinases (metabolism)
• Models, Molecular
• Structure-Activity Relationship
• Substrate Specificity