Bioorganic and Medicinal Chemistry p. 5402 - 5422 (2006)
Update date:2022-08-05
Topics:
Nakatani, Shingo
Ikura, Masahiro
Yamamoto, Shingo
Nishita, Yoshitaka
Itadani, Satoshi
Habashita, Hiromu
Sugiura, Tsuneyuki
Ogawa, Koji
Ohno, Hiroyuki
Takahashi, Kanji
Nakai, Hisao
Toda, Masaaki
A series of N-benzoyl 4-aminobutyric acid hydroxamate analogs were synthesized and evaluated as matrix metalloproteinase inhibitors. Synthetic work was focused on the chemical modification of the 4-aminobutyric acid part using easily available starting materials. As such, chemical modification was carried out using commercially available starting materials such as 4-aminobutyric acid, (+)- and (-)-malic acid, and d- and l-glutamic acid derivatives. Among the compounds tested, N-[4-(benzofuran-2-yl)benzoyl] 4-amino-4S-hydroxymethylbutyric acid hydroxamates derived from l-glutamic acid demonstrated more potent inhibitory activity against MMP-2 and MMP-9 compared with the corresponding 2S-hydroxy analogs or 3S-hydroxy analogs, respectively, which were derived from (-)-malic acid. Structure-activity relationship study is presented.
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