期刊
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷 25, 期 12, 页码 2523-2526出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2015.04.043
关键词
Metabotropic glutamate receptor; Fluorine; Amino-acids; Cyclopropane; Phosphonic acid
资金
- INSA Rouen
- Rouen University
- CNRS
- EFRD
- LabexSynOrg [ANR-11-LABX-0029]
- Region Haute-Normandie (Crunch Network)
- EFRD [EFRD 32819, 33236, 33091]
- IS:CE-Chem project
- LabexSynOrg
- Fondation Recherche Medicale [DEQ20130326522]
- Agence Nationale de la Recherche [ANR-13-BSV1-006]
- Ministere de l'Education Nationale et de la Recherche
- Fondation Recherche Medicale (FRM) [FDT20140931071]
- Centre National de la Recherche Scientifique (CNRS)
- Interreg IV A France(Channel)-England Program
The four stereoisomers of 1-amino-2-fluoro-2-(phosphonomethyl) cyclopropane-1-carboxylic acid (FAP4) were synthesized via diastereoselective Rh(II)-catalysed cyclopropanation of a phosphonylated fluoroalkene. Different isomers of FAP4 and the corresponding non-fluorinated analogs showed a similar pharmacological profile against the isoforms of metabotropic glutamate receptor (mGluR). Within the fluorinated series, (-)-(Z)-FAP4 and (-)-(E)-FAP4 demonstrated the highest agonist activity against mGlu4 (EC50 0.10 mu M). Our results suggest that fluorocyclopropanes bearing an amino-acid function can be suitable for the development of potent conformationally restricted mGluR agonists. (C) 2015 Elsevier Ltd. All rights reserved.
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