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.
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.
Marinozzi
Maura
M
Dipartimento di Chimica e Tecnologia del Farmaco, Università di Perugia, Via del Liceo, 1- I-06123 Perugia, Italy.
Serpi
Michaela
M
Amori
Laura
L
Gavilan Diaz
Monica
M
Costantino
Gabriele
G
Meyer
Udo
U
Flor
Peter J
PJ
Gasparini
Fabrizio
F
Heckendorn
Roland
R
Kuhn
Rainer
R
Giorgi
Gianluca
G
Hermit
Mette Brunsgaard
MB
Thomsen
Christian
C
Pellicciari
Roberto
R
D000818:Animals; D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D051381:Rats; D018094:Receptors, Metabotropic Glutamate / Q000819:agonists*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C520296:(2S)-2-(2'-phosphono-3'-phenylcyclopropyl)glycine; D003521:Cyclopropanes; D008024:Ligands; D018094:Receptors, Metabotropic Glutamate; D005998:Glycine