Synthesis of Oxadiazolidinedione Derivatives as Quisqualic Acid Analogues and Their Evaluation at a Quisqualate-Sensitized Site in the Rat Hippocampus

S Venkatraman, R J Roon, M K Schulte, J F Koerner, R L Johnson

J Med Chem. 1994 Nov 11;37(23):3939-46.

PMID: 7966155

Abstract:

The ability of quisqualic acid (1) to sensitize neurons to depolarization by omega-phosphono alpha-amino acid analogues of excitatory amino acids is a highly specific phenomenon and is termed the QUIS effect. In an attempt to elucidate the structure-activity relationships for this sensitization, analogues 2-6 of quisqualic acid have been synthesized. Compounds 4, 5, and 6 showed no quisqualate sensitization with respect to L-2-amino-6-phosphonohexanoic acid (L-AP6), while compounds 2 and 3 were 1/10 and 1/1000, respectively, as active as quisqualic acid in sensitizing neurons toward L-AP6.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP126253574	L-(+)-2-Amino-6-phosphonohexanoic acid		126253-57-4	Price
AP5662759	6-Phosphonohexanoic acid		5662-75-9	Price