Isosterism among analogues of torasemide: Conformational, electronic and lipophilic properties

The structures, electronic (charges, molecular electrostatic potential, molecular orbitals) and lipophilic properties of three isostere analogues of torasemide were determined and the influence of the replacement of the sulfonyl urea group on the conformation and electronic properties of the molecules is discussed. Lipophilicity of the compounds seems to be the most discriminating property along the series and affects their pharmacological activities. (C) 2000 Editions scientifiques et medicales Elsevier SAS.