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Synthesis and inhibitory activities at mGluRs of 3-alkylated and N-alkylated cyclopentyl-glutamate analogues

Journal Article


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Abstract


  • The conformationally restricted glutamate analogues, 3-alkyl-1-amino-2-cyclopentene-1,3-dicarboxylates and N-alkylated analogues have been prepared in a regioselective and diastereoselective manner. From the biological studies of the 3-alkylated analogues, compound 13b was found to be the most potent antagonist (IC50 7.7 μM) at mGluR2. Amongst the N-alkylated analogues, compound 20 was found to be a partial agonist (EC50 9.5 μM) and as well as an antagonist (IC50 47 μM) at mGluR2.

UOW Authors


  •   Ung, Alison T. (external author)
  •   Pyne, Stephen
  •   Bischoff, Francois (external author)
  •   Lesage, A S. (external author)
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)

Publication Date


  • 2013

Citation


  • Ung, A. T., Pyne, S. G., Bischoff, F., Lesage, A. S. J., Skelton, B. W. & White, A. H. (2013). Synthesis and inhibitory activities at mGluRs of 3-alkylated and N-alkylated cyclopentyl-glutamate analogues. Tetrahedron, 69 (12), 2577-2587.

Scopus Eid


  • 2-s2.0-84874113821

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1726&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/713

Number Of Pages


  • 10

Start Page


  • 2577

End Page


  • 2587

Volume


  • 69

Issue


  • 12

Abstract


  • The conformationally restricted glutamate analogues, 3-alkyl-1-amino-2-cyclopentene-1,3-dicarboxylates and N-alkylated analogues have been prepared in a regioselective and diastereoselective manner. From the biological studies of the 3-alkylated analogues, compound 13b was found to be the most potent antagonist (IC50 7.7 μM) at mGluR2. Amongst the N-alkylated analogues, compound 20 was found to be a partial agonist (EC50 9.5 μM) and as well as an antagonist (IC50 47 μM) at mGluR2.

UOW Authors


  •   Ung, Alison T. (external author)
  •   Pyne, Stephen
  •   Bischoff, Francois (external author)
  •   Lesage, A S. (external author)
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)

Publication Date


  • 2013

Citation


  • Ung, A. T., Pyne, S. G., Bischoff, F., Lesage, A. S. J., Skelton, B. W. & White, A. H. (2013). Synthesis and inhibitory activities at mGluRs of 3-alkylated and N-alkylated cyclopentyl-glutamate analogues. Tetrahedron, 69 (12), 2577-2587.

Scopus Eid


  • 2-s2.0-84874113821

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1726&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/713

Number Of Pages


  • 10

Start Page


  • 2577

End Page


  • 2587

Volume


  • 69

Issue


  • 12