2,3-Ethylene- and 2,3-trimethylene-bridged analogues of the group III metabotropic glutamate receptor ligand 2-amino-4-phosphonobutanoic acid

Rodney L Johnson, Kolluri S S P Rao

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

The racemic trans- and cis-isomers of 1-amino-2-phosphonomethyl- cyclobutanecarboxylic acid (5 and 6) and 1-amino-2-phosphonomethyl- cyclopentanecarboxylic acid (7 and 8) were synthesized as extensions of the mGluR4 agonists trans- and cis-1-amino-2-phosphonomethyl-cyclopropanecarboxylic acid (3 and 4). Although the methylene bridge in 3 and 4 allows for retention of affinity toward the mGluR4 receptor, increasing the bridging unit to the ethylene group as in 5 and 6 or to the trimethylene group as in 7 and 8 introduces sufficient steric hindrance to eliminate affinity for the mGluR4 receptor.

Original languageEnglish (US)
Pages (from-to)57-60
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume15
Issue number1
DOIs
StatePublished - Jan 3 2005

Keywords

  • AP4
  • Conformational analogues
  • mGluR4

Fingerprint Dive into the research topics of '2,3-Ethylene- and 2,3-trimethylene-bridged analogues of the group III metabotropic glutamate receptor ligand 2-amino-4-phosphonobutanoic acid'. Together they form a unique fingerprint.

  • Cite this