Design, synthesis and structure–activity relationship of a series of arginine aldehyde factor Xa inhibitors. Part 1: structures based on the ( )-Arg-Gly-Arg tripeptide sequence

A series of arginine aldehyde inhibitors was designed as transition state (TS) analogues based on the known factor Xa specific substrate Cbz- -Arg-Gly-Arg-pNA. BnSO2-( )Arg-Gly-Arg-H (20) was found to be the most potent and selective inhibitor of factor Xa and prothrombinase activity in this series.