Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2'-phosphono-3'-phenylcyclopropyl)glycine, the first class of 3'-substituted trans C1'-2'-2-(2'-phosphonocyclopropyl)glycines.

Maura Marinozzi, Michaela Serpi, Laura Amori, Monica Gavilan Diaz, Gabriele Costantino, Udo Meyer, Peter J Flor, Fabrizio Gasparini, Roland Heckendorn, Rainer Kuhn, Gianluca Giorgi, Mette Brunsgaard Hermit, Christian Thomsen, Roberto Pellicciari

Index: Bioorg. Med. Chem. 15 , 3161-70, (2007)

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Abstract

Four stereoisomers of (2S)-2-(2'-phosphono-3'-phenylcyclopropyl)glycine were synthesized by a stereocontrolled synthetic procedure and evaluated as mGluRs ligands. The (2S,1'R,2'S,3'R)-isomer (PPCG-2) showed to be a group III mGluRs selective ligand endowed with a moderate potency as mGluR4/mGluR6 agonist.