New 2-sulfonamidothiazoles substituted at C-4: synthesis of polyoxygenated aryl derivatives and in vitro evaluation of antifungal activity

Autor:	Stephane Larrouture, Jean-Michel Léger, Arlette Neveu, Gérard Deffieux, Pierre Beuchet, Martine Varache-Lembège, A. Nuhrich, Joseph Vercauteren
Rok vydání:	1999
Předmět:	Pharmacology Econazole Stereochemistry Aryl Organic Chemistry Ether General Medicine Tautomer Chemical synthesis chemistry.chemical_compound chemistry Drug Discovery Lipophilicity medicine Moiety Mulliken population analysis medicine.drug
Zdroj:	European Journal of Medicinal Chemistry. 34:773-779
ISSN:	0223-5234
DOI:	10.1016/s0223-5234(99)00215-9
Popis:	Polymethoxylated and polyhydroxylated derivatives of 2-amino-4-arylthiazoles bearing a halogenobenzenesulfonamide moiety at position 2 were synthesized as azole antifungal analogues. X-ray crystallography studies revealed the predominance of the 2-imino-2,3-dihydrothiazole form in the amino/imino tautomerism. In vitro assays against various pathogenic fungal strains (Candida and Trichophyton species) showed no activity in comparison to econazole as reference. These results are discussed on the basis of the estimated global lipophilicity of the molecules (Rekker's method) and the π-electron distribution (Mulliken population analysis, AM1 method) within the five-membered heterocycle.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f4d9b3349e4a6957c90154699b959642 https://doi.org/10.1016/s0223-5234(99)00215-9 Zobrazit plný text záznamu Full Text from ScienceDirect