title: A cyclopent-2-enecarbonyl group mimics proline at the P2 position of prolyl oligopeptidase inhibitors.
abstract: With the aim to replace the natural amino acid proline by a proline mimetic structure, a cyclopent-2-enecarbonyl moiety was studied at the P2 position of prolyl oligopeptidase (POP) inhibitors. The cyclopent-2-enecarbonyl moiety proved to be an excellent proline mimetic at the P2 position of POP inhibitors. The replacement is particularly useful when increased lipophilicity is needed.
authors.affiliation: Department of Pharmaceutical Chemistry, University of Kuopio, P.O. Box 1627, FI-70211 Kuopio, Finland. Elina.Jarho@uku.fi
authors.forename: Elina M
authors.initials: EM
authors.lastname: Jarho
authors.forename: Jarkko I
authors.initials: JI
authors.lastname: Venäläinen
authors.forename: Juhani
authors.initials: J
authors.lastname: Huuskonen
authors.forename: Johannes A M
authors.initials: JA
authors.lastname: Christiaans
authors.forename: J Arturo
authors.initials: JA
authors.lastname: Garcia-Horsman
authors.forename: Markus M
authors.initials: MM
authors.lastname: Forsberg
authors.forename: Tomi
authors.initials: T
authors.lastname: Järvinen
authors.forename: Jukka
authors.initials: J
authors.lastname: Gynther
authors.forename: Pekka T
authors.initials: PT
authors.lastname: Männistö
authors.forename: Erik A A
authors.initials: EA
authors.lastname: Wallén
mesh_terms: D020003:1-Octanol; D000818:Animals; D001921:Brain / Q000187:drug effects / Q000201:enzymology; D002021:Buffers; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D066298:In Vitro Techniques; D018716:Molecular Mimicry; D011392:Proline / Q000737:chemistry*; D000085822:Prolyl Oligopeptidases; D012697:Serine Endopeptidases / Q000378:metabolism*; D015842:Serine Proteinase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D012995:Solubility; D013329:Structure-Activity Relationship; D013552:Swine
chemical_list: D002021:Buffers; D003517:Cyclopentanes; D015842:Serine Proteinase Inhibitors; D011392:Proline; D012697:Serine Endopeptidases; D000085822:Prolyl Oligopeptidases; D020003:1-Octanol