title: Synthesis and antifungal activity of bile acid-derived oxazoles.
abstract: Peracetylated bile acids (1a-g) were used as starting materials for the preparation of fourteen new derivatives bearing an oxazole moiety in their side chain (6a-g, 8a-g). The key step for the synthetic path was a Dakin-West reaction followed by a Robinson-Gabriel cyclodehydration. A simpler model oxazole (12) was also synthesized. The antifungal activity of the new compounds (6a-g) as well as their starting bile acids (1a-g) was tested against Candida albicans. Compounds 6e and 6g showed the highest percentages of inhibition (63.84% and 61.40% at 250 μg/mL respectively). Deacetylation of compounds 6a-g, led to compounds 8a-g which showed lower activities than the acetylated derivatives.
authors.affiliation: UMYMFOR - Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 3° Piso, (1428) Buenos Aires, Argentina.
authors.forename: Lucía R
authors.initials: LR
authors.lastname: Fernández
authors.affiliation: Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, CP2000, Rosario, Argentina.
authors.forename: Laura
authors.initials: L
authors.lastname: Svetaz
authors.affiliation: Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, CP2000, Rosario, Argentina.
authors.forename: Estefanía
authors.initials: E
authors.lastname: Butassi
authors.affiliation: Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, CP2000, Rosario, Argentina.
authors.forename: Susana A
authors.initials: SA
authors.lastname: Zacchino
authors.affiliation: UMYMFOR - Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 3° Piso, (1428) Buenos Aires, Argentina.
authors.forename: Jorge A
authors.initials: JA
authors.lastname: Palermo
authors.affiliation: UMYMFOR - Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 3° Piso, (1428) Buenos Aires, Argentina. Electronic address: msanchez@qo.fcen.uba.ar.
authors.forename: Marianela
authors.initials: M
authors.lastname: Sánchez
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001647:Bile Acids and Salts / Q000737:chemistry*; D002176:Candida albicans / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D008970:Molecular Weight; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000935:Antifungal Agents; D001647:Bile Acids and Salts; D010080:Oxazoles
keywords: Bile acids; Candida albicans; Dakin–West reaction; Oxazoles