Novel potent 5-HT(3) receptor ligands based on the pyrrolidone structure. Effects of the quaternization of the basic nitrogen on the interaction with 5-HT(3) receptor
The results of a comprehensive structure-affinity relationship study on the effect of the quaternization (i.e., N-methylation) of structurally different ligands in the classes of tropane and quinuclidine derivatives are described. This study shows that the effects of the quaternization of the basic...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2002-08, Vol.10 (8), p.2681-2691 |
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| creator | Cappelli, Andrea Gallelli, Andrea Braile, Carlo Anzini, Maurizio Vomero, Salvatore Mennuni, Laura Makovec, Francesco Menziani, M Cristina De Benedetti, Pier G Donati, Alessandro Giorgi, Gianluca |
| description | The results of a comprehensive structure-affinity relationship study on the effect of the quaternization (i.e., N-methylation) of structurally different ligands in the classes of tropane and quinuclidine derivatives are described. This study shows that the effects of the quaternization of the basic nitrogen of these 5-HT(3) receptor ligands appear to be strictly structure-dependent suggesting that different binding modes are operative at 5-HT(3) receptor binding site. The different effect of the quaternization of the basic nitrogen of structurally different ligands were rationalized in terms of the interaction with the receptor by means of the combined use of experimental techniques (X-ray diffraction and NMR studies) and computational simulation studies. |
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| ispartof | Bioorganic & medicinal chemistry, 2002-08, Vol.10 (8), p.2681-2691 |
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| subjects | Animals Brain - cytology Brain - metabolism Crystallography, X-Ray Ligands Magnetic Resonance Spectroscopy Male Molecular Structure Protein Binding Pyrrolidinones - chemical synthesis Pyrrolidinones - pharmacology Quaternary Ammonium Compounds Quinuclidines - chemical synthesis Quinuclidines - pharmacology Rats Rats, Wistar Receptors, Serotonin - chemistry Receptors, Serotonin, 5-HT3 Serotonin Antagonists - chemical synthesis Structure-Activity Relationship Tropanes - chemical synthesis Tropanes - pharmacology |
| title | Novel potent 5-HT(3) receptor ligands based on the pyrrolidone structure. Effects of the quaternization of the basic nitrogen on the interaction with 5-HT(3) receptor |
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