Cinnamylindoline Derivatives: Synthesis and Factor Xa (FXa) Inhibitory Activities

Tetsuji Noguchi; Naoki Tanaka; Toyoki Nishimata; Riki Goto; Miho Hayakawa; Atsuhiro Sugidachi; Taketoshi Ogawa; Fumitoshi Asai; Koichi Fujimoto

doi:10.1248/cpb.55.1494

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Cinnamylindoline Derivatives: Synthesis and Factor Xa (FXa) Inhibitory Activities

Tetsuji Noguchi, Naoki Tanaka, Toyoki Nishimata, Riki Goto, Miho Hayakawa, Atsuhiro Sugidachi, Taketoshi Ogawa, Fumitoshi Asai, Koichi Fujimoto

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Keywords: factor Xa inhibitory activity, cinnamylindoline derivative, anticoagulant

JOURNAL FREE ACCESS

2007 Volume 55 Issue 10 Pages 1494-1504

DOI https://doi.org/10.1248/cpb.55.1494

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Abstract

A series of cinnamylindoline derivatives were synthesized, and their factor Xa (FXa) inhibitory activities and selectivity over trypsin were evaluated. Among them, some novel derivatives showed potent FXa inhibitory activities and good selectivity over trypsin. Especially, (E)-2-{5-[1-(acetimidoyl)piperidin-4-yloxy]-2-[2-(5-amidino-2-hydroxyphenyl)ethen-1-yl]indolin-1-ylsulfonyl}acetic acid (22f) having 2-hydroxycinnamyl moiety exhibited the most potent FXa inhibitory activity in vitro. Furthermore, 22f also exhibited potent anticoagulant activities in vitro.

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