Artículo
Fernández, L.R.; Svetaz, L.; Butassi, E.; Zacchino, S.A.; Palermo, J.A.; Sánchez, M. "Synthesis and antifungal activity of bile acid-derived oxazoles" (2016) Steroids. 108:68-76
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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. © 2016 Elsevier Inc. All rights reserved.
Registro:
| Documento: | Artículo |
| Título: | Synthesis and antifungal activity of bile acid-derived oxazoles |
| Autor: | Fernández, L.R.; Svetaz, L.; Butassi, E.; Zacchino, S.A.; Palermo, J.A.; Sánchez, M. |
| Filiación: | UMYMFOR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 3<sup>o</sup>Piso, Buenos Aires, 1428, Argentina Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario, CP2000, Argentina |
| Palabras clave: | Bile acids; Candida albicans; Dakin-West reaction; Oxazoles; amphotericin B; antifungal agent; bile acid; methyl 2 (2,5 dimethyloxazol 4 yl)acetate; methyl [5 methyl 2 (3alpha acetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,12alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,12alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,6alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,6alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,6alpha,7alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,6alpha,7alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,7alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,7alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,7alpha,12alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,7alpha,12alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,7beta diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,7beta dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; methyl [5 methyl 2 (3alpha,hydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate; oxazole derivative; unclassified drug; antifungal agent; bile acid; oxazole derivative; antifungal activity; Article; Candida albicans; covalent bond; deacetylation; drug mechanism; drug synthesis; fungal strain; fungus growth; growth inhibition; lipophilicity; nonhuman; chemistry; drug effects; molecular weight; synthesis; Antifungal Agents; Bile Acids and Salts; Candida albicans; Chemistry Techniques, Synthetic; Molecular Weight; Oxazoles |
| Año: | 2016 |
| Volumen: | 108 |
| Página de inicio: | 68 |
| Página de fin: | 76 |
| DOI: | http://dx.doi.org/10.1016/j.steroids.2016.01.014 |
| Título revista: | Steroids |
| Título revista abreviado: | Steroids |
| ISSN: | 0039128X |
| CODEN: | STEDA |
| CAS: | amphotericin B, 1397-89-3, 30652-87-0; Antifungal Agents; Bile Acids and Salts; Oxazoles |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v108_n_p68_Fernandez |
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Citas:
---------- APA ----------
Fernández, L.R., Svetaz, L., Butassi, E., Zacchino, S.A., Palermo, J.A. & Sánchez, M. (2016) . Synthesis and antifungal activity of bile acid-derived oxazoles. Steroids, 108, 68-76.http://dx.doi.org/10.1016/j.steroids.2016.01.014
---------- CHICAGO ----------
Fernández, L.R., Svetaz, L., Butassi, E., Zacchino, S.A., Palermo, J.A., Sánchez, M. "Synthesis and antifungal activity of bile acid-derived oxazoles" . Steroids 108 (2016) : 68-76.http://dx.doi.org/10.1016/j.steroids.2016.01.014
---------- MLA ----------
Fernández, L.R., Svetaz, L., Butassi, E., Zacchino, S.A., Palermo, J.A., Sánchez, M. "Synthesis and antifungal activity of bile acid-derived oxazoles" . Steroids, vol. 108, 2016, pp. 68-76.http://dx.doi.org/10.1016/j.steroids.2016.01.014
---------- VANCOUVER ----------
Fernández, L.R., Svetaz, L., Butassi, E., Zacchino, S.A., Palermo, J.A., Sánchez, M. Synthesis and antifungal activity of bile acid-derived oxazoles. Steroids. 2016;108:68-76.http://dx.doi.org/10.1016/j.steroids.2016.01.014
