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Synthesis and Structure-Activity Relationship Analysis of Caffeic Acid Amides as Selective Matrix Metalloproteinase Inhibitors

Synthesis and Structure-Activity Relationship Analysis of Caffeic 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

Bioorg Med Chem Lett. 2013 Mar 1;23(5):1206-11.

PMID: 23375794

Abstract:

Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42416004	MMP-2/MMP-9 Substrate I, Fluorogenic			Price

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