Novel pyrrolinones as N-methyl-d-aspartate receptor antagonists
| Autor: | Hans-Dietrich Stachel, G. Hoefner, Hermann Poschenrieder, Peter Mayer |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Pharmacology
chemistry.chemical_classification Binding Sites Molecular Structure Diazomethane Stereochemistry Organic Chemistry Glycine General Medicine Glycine receptor antagonist N-methyl-D-aspartate Receptor Antagonists Oxime Receptors N-Methyl-D-Aspartate Tautomer Chemical synthesis Pyrrole derivatives Nitrone Structure-Activity Relationship chemistry.chemical_compound chemistry Drug Discovery Pyrroles Glycine receptor |
| Zdroj: | European Journal of Medicinal Chemistry. 40:391-400 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2004.11.010 |
| Popis: | A series of oximes, deriving from 2-arylidene-pyrroline-3,4-diones (7, 8, 22, 23) has been prepared. The presence of tautomers in their solutions has been established by spectroscopic means. The compounds reacted with diazomethane chiefly by N-methylation forming nitrones (10, 11). The analogously prepared 2-arylidene-4-nitropyrrolin-3-ones (12, 13, 24, 25), formally derived from nitrotetramic acids, yielded nitronic acid esters (14, 15, 26) upon reaction with diazomethane. The structures were elucidated by spectral evidence and-in the case of compounds 10 and 20b-by X-ray diffraction analysis. The binding affinity of some of the new compounds toward the N-methyl-d-aspartate (NMDA) (glycine site) receptor has been measured thus providing the basis for further structure-activity relationship studies. Oxime 8b showed the highest binding potency (Ki= 9.2 microM). |
| Databáze: | OpenAIRE |
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