116381-08-9Relevant academic research and scientific papers
Design and synthesis of novel metalloproteinase inhibitors
Nakatani, Shingo,Ikura, Masahiro,Yamamoto, Shingo,Nishita, Yoshitaka,Itadani, Satoshi,Habashita, Hiromu,Sugiura, Tsuneyuki,Ogawa, Koji,Ohno, Hiroyuki,Takahashi, Kanji,Nakai, Hisao,Toda, Masaaki
, p. 5402 - 5422 (2007/10/03)
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.
