title: Synthesis and dipeptidyl peptidase inhibition of N-(4-substituted-2,4-diaminobutanoyl)piperidines.
abstract: In this paper, we report the synthesis of diastereomerically pure N-(4-substituted-2,4-diaminobutanoyl)piperidines. These compounds were prepared to investigate the influence of the 4-substitution on the dipeptidyl peptidase II (DPP II) activity and selectivity of the parent N-(2,4-diaminobutanoyl)piperidine. The (4S)-methyl compound showed subnanomolar inhibition, comparable with the parent compound. The (4R)-methyl group or bigger substituents decreased the activity.
authors.affiliation: Laboratory of Medicinal Chemistry University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium.
authors.forename: Anna
authors.initials: A
authors.lastname: Soroka
authors.forename: Pieter
authors.initials: P
authors.lastname: Van der Veken
authors.forename: Ingrid
authors.initials: I
authors.lastname: De Meester
authors.forename: Anne-Marie
authors.initials: AM
authors.lastname: Lambeir
authors.forename: Marie-Berthe
authors.initials: MB
authors.lastname: Maes
authors.forename: Simon
authors.initials: S
authors.lastname: Scharpé
authors.forename: Achiel
authors.initials: A
authors.lastname: Haemers
authors.forename: Koen
authors.initials: K
authors.lastname: Augustyns
mesh_terms: D000586:Amination; D004152:Dipeptidyl-Peptidases and Tripeptidyl-Peptidases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D010880:Piperidines; D011480:Protease Inhibitors; C032727:piperidine; D004152:Dipeptidyl-Peptidases and Tripeptidyl-Peptidases; C100151:dipeptidyl peptidase II