title: Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.
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.
authors: Jiangsu Key Laboratory for High Technology Research of TCM Formulae, Nanjing University of Chinese Medicine, Nanjing, Jiangsu 210046, China.
authors: Zhi-Hao
authors: ZH
authors: Shi
authors: Nian-Guang
authors: NG
authors: Li
authors: Qian-Ping
authors: QP
authors: Shi
authors: Hao
authors: H
authors: Tang
authors: Yu-Ping
authors: YP
authors: Tang
authors: Wei
authors: W
authors: Li
authors: Lian
authors: L
authors: Yin
authors: Jian-Ping
authors: JP
authors: Yang
authors: Jin-Ao
authors: JA
authors: Duan
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002109:Caffeic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D061965:Matrix Metalloproteinase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D002109:Caffeic Acids; D061965:Matrix Metalloproteinase Inhibitors; C040048:caffeic acid