Aminoindan-1,5-dicarboxylic

In the laboratory of D. Ma, the asymmetric synthesis of several metabotropic glutamate receptor antagonists derived from a-alkylated phenylglycines was undertaken. The preparation of (S)-1-aminoindan-1,5-dicarboxylic acid (AIDA) started with the Perkin reaction of 3-bromobenzaldehyde and malonic acid. The resulting ( )-cinnamic acid derivative was hydrogenated and the following intramolecular Friedel-Crafts acylation afforded the corresponding indanone, which was then converted to (S)-AIDA. 

Natalini, B., Marinozzi, M., Bade, K., Sardella, R.,Thomsen, C., Pellicciari, R. Preparative resolution of 1-aminoindan-1,5-dicarboxylic acid (AIDA) by chiral ligand-exchange chromatography. Chirality, 2004,16, 314-317. 

Moroni F, Lombardi G, Thomsen C et al (1997) Pharmacological characterization of 1-aminoindan-l, 5-dicarboxylic acid, AIDA, a potent mGluRl antagonist. J Pharmacol Exp Ther 281 721-9... 

Antagonists of metabotropic glutamate receptors and G-protein-coupled receptors associated with various neurodegenerate diseases have been prepared by proline-catalyzed direct a-amination reactions (Scheme 2.30) [7c]. Both, indane carbaldehyde 10 and analogous compounds having an ester functionality [leading to l-aminoindan-l,5-dicarboxylic acid (AIDA)] and or a phosphonate substituent [(RS)-l-amino-5-phosphonoindan-l-carboxylic acid APICA], all reacted with di-... 

Pellicciari, R., Luneia, R., Costantino, G., Marinozzi, M., Natalini, B., Jakobsen, P., Kanstrup, A., Lombardi, G., Moroni, F., Thomsen, C., 1995. l-Aminoindan-l,5-dicarboxylic acid a novel antagonist at phospholipase C-linked metabotropic glutamate receptors. J. Med. Chem. 38, 3717-3719. 

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