Synthesis and preliminary biological evaluation of (2S,1'R,2'S)- and (2S,1'S,2'R)-2-(2'-phosphonocyclopropyl)glycines, two novel conformationally constrained l-AP4 analogues

Laura Amori; Michaela Serpi; Maura Marinozzi; Gabriele Costantino; Monica Gavilan Diaz; Mette Brunsgaard Hermit; Christian Thomsen; Roberto Pellicciari

doi:10.1016/j.bmcl.2005.09.014

Synthesis and preliminary biological evaluation of (2S,1'R,2'S)- and (2S,1'S,2'R)-2-(2'-phosphonocyclopropyl)glycines, two novel conformationally constrained l-AP4 analogues

Bioorg Med Chem Lett. 2006 Jan 1;16(1):196-9. doi: 10.1016/j.bmcl.2005.09.014. Epub 2005 Oct 5.

Authors

Laura Amori¹, Michaela Serpi, Maura Marinozzi, Gabriele Costantino, Monica Gavilan Diaz, Mette Brunsgaard Hermit, Christian Thomsen, Roberto Pellicciari

Affiliation

¹ Dipartimento di Chimica e Tecnologia del Farmaco, Università di Perugia, Via del Liceo, 1-06123 Perugia, Italy.

PMID: 16213710
DOI: 10.1016/j.bmcl.2005.09.014

Abstract

Two novel constrained l-AP4 analogues, (2S,1'R,2'S)- and (2S,1'S,2'R)-2-(2'-phosphonocyclopropyl)glycines (7) and (8), were synthesized and evaluated as mGluR ligands. Compound 7 showed to be a group III mGluRs agonist with micromolar activity.

MeSH terms

Animals
CHO Cells
Cell Line
Cricetinae
Glutamic Acid / chemistry
Glycine / chemistry*
Kinetics
Ligands
Models, Chemical
Molecular Conformation
Propionates / chemical synthesis*
Propionates / chemistry*
Protein Binding
Protein Conformation
Receptors, Metabotropic Glutamate / chemistry*
Stereoisomerism

Substances

2-amino-4-phosphono-propinate
Ligands
Propionates
Receptors, Metabotropic Glutamate
Glutamic Acid
Glycine