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Synthesis and pharmacological evaluation of conformationally constrained glutamic acid higher homologues.
- Source :
-
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2016 Nov 15; Vol. 24 (22), pp. 5741-5747. Date of Electronic Publication: 2016 Sep 12. - Publication Year :
- 2016
-
Abstract
- Homologation of glutamic acid chain together with conformational constraint is a commonly used strategy to achieve selectivity towards different types of glutamate receptors. In the present work, starting from two potent and selective unnatural amino acids previously developed by us, we investigated the effects on the activity/selectivity profile produced by a further increase in the distance between the amino acidic moiety and the distal carboxylate group. Interestingly, the insertion of an aromatic ring as a spacer produced a low micromolar affinity NMDA ligand that might represent a lead for the development of a new class of NMDA antagonists.<br /> (Copyright © 2016 Elsevier Ltd. All rights reserved.)
- Subjects :
- Animals
Dose-Response Relationship, Drug
Excitatory Amino Acid Antagonists chemistry
Glutamic Acid chemical synthesis
Glutamic Acid chemistry
Molecular Conformation
Rats
Receptors, N-Methyl-D-Aspartate metabolism
Structure-Activity Relationship
Excitatory Amino Acid Antagonists chemical synthesis
Excitatory Amino Acid Antagonists pharmacology
Glutamic Acid analogs & derivatives
Glutamic Acid pharmacology
Receptors, N-Methyl-D-Aspartate antagonists & inhibitors
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3391
- Volume :
- 24
- Issue :
- 22
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27658797
- Full Text :
- https://doi.org/10.1016/j.bmc.2016.09.029