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Design, Synthesis and Biological Evaluation of Caffeic Acid Amides as Selective MMP ‐2 and MMP ‐9 Inhibitors
Author(s) -
Shi ZhiHao,
Li NianGuang,
Shi QianPing,
Tang Hao,
Tang YuPing,
Li Wei,
Yin Lian,
Yang JianPing,
Duan JinAo
Publication year - 2012
Publication title -
drug development research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.582
H-Index - 60
eISSN - 1098-2299
pISSN - 0272-4391
DOI - 10.1002/ddr.21038
Subject(s) - caffeic acid , matrix metalloproteinase , chemistry , selectivity , caffeic acid phenethyl ester , biochemistry , inhibitory postsynaptic potential , docking (animal) , stereochemistry , pharmacology , enzyme , structure–activity relationship , medicine , in vitro , antioxidant , catalysis , nursing
trategy, Management and Health Policy Preclinical ResearchA series of caffeic acid amides with extended P 1′ groups were synthesized and tested for their inhibitory activities on matrix metalloproteinase ( MMP )‐1, MMP ‐2, and MMP ‐9. Compound 3f showed considerable inhibitory activities against MMP ‐2, MMP ‐9, and best selectivity over MMP ‐1. Preliminary structure–activity relationship analysis and docking studies indicated that caffeic acid amides with electron‐donating groups at p ‐position of amino phenyl group showed better inhibitory activities and selectivity than those with electron‐withdrawing groups. The findings of this study would provide information for the exploitation and utilization of caffeic acid as MMP inhibitor for metastatic tumor treatment.