A Cyclopent-2-enecarbonyl Group Mimics Proline at the P2 Position of Prolyl Oligopeptidase Inhibitors

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 inh...

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Bibliographic Details
Published in:Journal of medicinal chemistry 2004-11, Vol.47 (23), p.5605-5607
Main Authors: Jarho, Elina M, Venäläinen, Jarkko I, Huuskonen, Juhani, Christiaans, Johannes A. M, Garcia-Horsman, J. Arturo, Forsberg, Markus M, Järvinen, Tomi, Gynther, Jukka, Männistö, Pekka T, Wallén, Erik A. A
Format: Article
Language:English
Subjects:
1-Octanol
Analytical, structural and metabolic biochemistry
Animals
Biological and medical sciences
Brain - drug effects
Brain - enzymology
Buffers
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Cyclopentanes - pharmacology
Enzymes and enzyme inhibitors
Fundamental and applied biological sciences. Psychology
Hydrolases
In Vitro Techniques
Medical sciences
Miscellaneous
Molecular Mimicry
Pharmacology. Drug treatments
Proline - chemistry
Serine Endopeptidases - metabolism
Serine Proteinase Inhibitors - chemical synthesis
Serine Proteinase Inhibitors - chemistry
Serine Proteinase Inhibitors - pharmacology
Solubility
Structure-Activity Relationship
Swine
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm049503w