71309-26-7Relevant academic research and scientific papers
Thieno[2,3-b]pyridinones as antagonists on the glycine site of the N- methyl-D-aspartate receptor - Binding studies, molecular modeling and structure-activity-relationships
Buchstaller,Siebert,Lyssy,Ecker,Krug,Berger,Gottschlich,Noe
, p. 3 - 14 (2000)
Within the frame of the synthesis of glycine antagonists, a series of novel thieno[2,3-b]pyridinones with substituted phenyl residues in position 5 were synthesised to investigate the importance of the torsion angle between the pyridinone skeleton and the phenyl ring for binding affinity. The parent compound, 4-hydroxy-5-phenylthieno[2,3-b]pyridine-6(7H)-one, and its thienyl analogue, exhibited highest potencies, whereas compounds with ortho- substituted aryl moleties in position 5 showed decreased activities. This seems to be due to unfavourable steric interactions and increased torsion angles between the thieno[2,3-b]pyridinone system and the aryl substituent in position 5. Further evidence is drawn by QSAR studies, which showed an inverse relationship between the size of the ortho-substituent and the binding affinity.
Synthesis of thieno[2,3-b]pyridinones acting as cytoprotectants and as inhibitors of [3H]glycine binding to the N-methyl-D-aspartate (NMDA) receptor
Buchstaller, Hans-Peter,Siebert, Carsten D.,Steinmetz, Ralf,Frank, Ina,Berger, Michael L.,Gottschlich, Rudolf,Leibrock, Joachim,Krug, Michael,Steinhilber, Dieter,Noe, Christian R.
, p. 864 - 871 (2007/10/03)
The standard glycine site antagonist of the N-methyl-D-aspartate (NMDA) receptor, 3-phenyl-4-hydroxyquinolin-2(1H)-one (21), was used as a template for bioisostere benzene/thiophene exchange. Phenylacetylation of aminothiophene carboxylic acid methyl este
