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ID: ALA1148427

Journal: Bioorg Med Chem Lett

Title: Diastereoselective synthesis and configuration-dependent activity of (3-substituted-cycloalkyl)glycine pyrrolidides and thiazolidides as dipeptidyl peptidase IV inhibitors.

Authors: Ashton WT, Dong H, Sisco RM, Doss GA, Leiting B, Patel RA, Wu JK, Marsilio F, Thornberry NA, Weber AE.

Abstract: A diastereoselective synthesis was used to prepare a series of (3-substituted-cyclopentyl and -cyclohexyl)glycine pyrrolidides and thiazolidides. The three chiral centers were generated in an unambiguous, stereochemically defined manner. Inhibitory activity was dependent on the configuration at each stereocenter and on the nature of the 3-substituent. In the cyclopentylglycine pyrrolidide series, high potency against dipeptidyl peptidase IV and good selectivity could be achieved.

CiteXplore: 15012982

DOI: 10.1016/j.bmcl.2003.12.013