Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

LM Simpkins, S Bolton, Z Pi, JC Sutton, C Kwon…

Index: Simpkins, Ligaya M.; Bolton, Scott; Pi, Zulan; Sutton, James C.; Kwon, Chet; Zhao, Guohua; Magnin, David R.; Augeri, David J.; Gungor, Timur; Rotella, David P.; Sun, Zhong; Liu, Yajun; Slusarchyk, William S.; Marcinkeviciene, Jovita; Robertson, James G.; Wang, Aiying; Robl, Jeffrey A.; Atwal, Karnail S.; Zahler, Robert L.; Parker, Rex A.; Kirby, Mark S.; Hamann, Lawrence G. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 23 p. 6476 - 6480

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Citation Number: 23

Abstract

The synthesis and structure–activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with β-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S, 3R)-2, 3- methanopyrrolidine based scaffold.

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