S. Collin, F. Moureau, M. Quintero, D. P. Vercauteren, G. Evrard, F. Durant
{"title":"Stereoelectronic Requirements of Benzamide 5ht(3) Antagonists - Comparison With D-2 Antidopaminergic Analogs","authors":"S. Collin, F. Moureau, M. Quintero, D. P. Vercauteren, G. Evrard, F. Durant","doi":"10.1039/P29950000077","DOIUrl":"https://doi.org/10.1039/P29950000077","url":null,"abstract":"Renzapride (I) and Tropapride (IV) are very similar substituted benzamides but are distinguishable by their pharmacological profile: the former is a potent 5HT(3) antagonist while the latter is a very active D-2 antidopaminergic drug. A combination of experimental methods (X-ray diffraction and H-1 NMR spectroscopy) and theoretical calculations (semiempirical molecular orbital AM1) were used to investigate the conformational space of three 5HT(3) antagonists: Renzapride (I, BRL24924), DAU6215 (II) and Ondansetron (III, GR38032). The analysis of their solid state conformations as well as their isolated state structures allows us to propose a 5HT(3) pharmacophoric model which is compared to the one previously reported for benzamide D-2 antagonists, represented by Tropapride (IV).","PeriodicalId":377825,"journal":{"name":"The Royal Society of Chemistry","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"1900-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"130722429","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}