Novel thrombin inhibitors that are based on a macrocyclic tripeptide motif

A series of macrocyclic α-keto amides containing the D-Phe-Pro-Arg (fPR) motif were synthesized and evaluated in vitro as inhibitors of human α-thrombin and bovine trypsin. Structure-function studies, relating ring size and modifications at the P3 and P1' positions to enzyme inhibition, are des...

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Published inBioorganic & medicinal chemistry letters Vol. 6; no. 24; pp. 2947 - 2952
Main Authors Greco, Michael N., Powell, Eugene T., Hecker, Leonard R., Andrade-Gordon, Patricia, Kauffman, Jack A., Lewis, Joan M., Ganesh, Venkatapathy, Tulinsky, Alexander, Maryanoff, Bruce E.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 17.12.1996
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Abstract A series of macrocyclic α-keto amides containing the D-Phe-Pro-Arg (fPR) motif were synthesized and evaluated in vitro as inhibitors of human α-thrombin and bovine trypsin. Structure-function studies, relating ring size and modifications at the P3 and P1' positions to enzyme inhibition, are described. An X-ray crystallo-graphic study was performed on a ternary complex formed from 3i, thrombin, and hirugen. A series of macrocyclic thrombin inhibitors ( 3 and 4) containing the D-Phe-Pro-Arg motif were synthesized and evaluated in vitro as inhibitors of human α-thrombin and bovine trypsin. An X-ray crystallographic study was performed on a complex formed from 3i (R(CH 2) 2Ph; m = 7; XO; ZCH 2), thrombin, and hirugen.
AbstractList A series of macrocyclic α-keto amides containing the D-Phe-Pro-Arg (fPR) motif were synthesized and evaluated in vitro as inhibitors of human α-thrombin and bovine trypsin. Structure-function studies, relating ring size and modifications at the P3 and P1' positions to enzyme inhibition, are described. An X-ray crystallo-graphic study was performed on a ternary complex formed from 3i, thrombin, and hirugen. A series of macrocyclic thrombin inhibitors ( 3 and 4) containing the D-Phe-Pro-Arg motif were synthesized and evaluated in vitro as inhibitors of human α-thrombin and bovine trypsin. An X-ray crystallographic study was performed on a complex formed from 3i (R(CH 2) 2Ph; m = 7; XO; ZCH 2), thrombin, and hirugen.
Author Maryanoff, Bruce E.
Greco, Michael N.
Kauffman, Jack A.
Lewis, Joan M.
Andrade-Gordon, Patricia
Tulinsky, Alexander
Powell, Eugene T.
Hecker, Leonard R.
Ganesh, Venkatapathy
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