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.
Wouters
J
J
Laboratory of Molecular Structure and Department of Pharmacy, Facultés Universitaires Notre Dame de la Paix, Namur, Belgium.
Michaux
C
C
Durant
F
F
Dogné
J M
JM
Delarge
J
J
Masereel
B
B
D000818:Animals; D003461:Crystallography; D004232:Diuretics / Q000737:chemistry* / Q000494:pharmacology; D007536:Isomerism; D008968:Molecular Conformation; D021281:Quantitative Structure-Activity Relationship; D051381:Rats; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology; D000077786:Torsemide
D004232:Diuretics; D013449:Sulfonamides; D000077786:Torsemide