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

J. Wouters; C. Michaux; F. Durant; Jean-Michel Dogne; J. Delarge; B. Masereel

doi:10.1016/S0223-5234(00)01174-0

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

J. Wouters, C. Michaux, F. Durant, Jean-Michel Dogne, J. Delarge, B. Masereel

Unit of theoretical and structural physico-chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	923-929
Number of pages	7
Journal	European Journal of Medicinal Chemistry
Volume	35
Issue number	10
DOIs	https://doi.org/10.1016/S0223-5234(00)01174-0
Publication status	Published - Oct 2000

Keywords

Animals
Crystallography
Diuretics
Isomerism
Molecular Conformation
Quantitative Structure-Activity Relationship
Rats
Sulfonamides

Access to Document

10.1016/S0223-5234(00)01174-0

Cite this

@article{c69c796f79b1481c8172616263154c13,

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

abstract = "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.",

keywords = "Animals, Crystallography, Diuretics, Isomerism, Molecular Conformation, Quantitative Structure-Activity Relationship, Rats, Sulfonamides",

author = "J. Wouters and C. Michaux and F. Durant and Jean-Michel Dogne and J. Delarge and B. Masereel",

year = "2000",

month = oct,

doi = "10.1016/S0223-5234(00)01174-0",

language = "English",

volume = "35",

pages = "923--929",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier",

number = "10",

}

TY - JOUR

T1 - Isosterism among analogues of torasemide

T2 - Conformational, electronic and lipophilic properties

AU - Wouters, J.

AU - Michaux, C.

AU - Durant, F.

AU - Dogne, Jean-Michel

AU - Delarge, J.

AU - Masereel, B.

PY - 2000/10

Y1 - 2000/10

N2 - 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.

AB - 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.

KW - Animals

KW - Crystallography

KW - Diuretics

KW - Isomerism

KW - Molecular Conformation

KW - Quantitative Structure-Activity Relationship

KW - Rats

KW - Sulfonamides

UR - http://www.scopus.com/inward/record.url?scp=0033729352&partnerID=8YFLogxK

U2 - 10.1016/S0223-5234(00)01174-0

DO - 10.1016/S0223-5234(00)01174-0

M3 - Article

C2 - 11121618

SN - 0223-5234

VL - 35

SP - 923

EP - 929

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 10

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this