Artículo
Siless, G.E.; Lozano, E.; Sánchez, M.; Mazzuca, M.; Sosa, M.A.; Palermo, J.A. "Preparation and antitrypanosomal activity of secochiliolide acid derivatives" (2013) Bioorganic and Medicinal Chemistry Letters. 23(17):4964-4967
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Abstract:
Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum bryoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 μg/mL. Six of the synthesized derivatives were also active with IC50's between 2 and 7 μg/mL which are comparable to that of the commercial drug benznidazole (2.5 μg/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule. © 2013 Elsevier Ltd. All rights reserved.
Registro:
| Documento: | Artículo |
| Título: | Preparation and antitrypanosomal activity of secochiliolide acid derivatives |
| Autor: | Siless, G.E.; Lozano, E.; Sánchez, M.; Mazzuca, M.; Sosa, M.A.; Palermo, J.A. |
| Filiación: | UMYMFOR-CONICET - Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, (1428), Buenos Aires, Argentina Laboratorio de Biología y Fisiología Celular Dr. Francisco Bertini, Instituto de Histología y Embriología, Universidad Nacional de Cuyo, Mendoza, Argentina Dpto. de Química, Facultad de Ciencias Naturales, Universidad Nacional de la Patagonia San Juan Bosco, Km 4, (9000), Comodoro Rivadavia, Chubut, Argentina Instituto de Ciencias Básicas (ICB), Universidad Nacional de Cuyo, Mendoza, Argentina |
| Palabras clave: | Nardophyllum bryoides trypanocidal activity; Secochiliolide acid; Trypanosoma cruzi; antitrypanosomal agent; benznidazole; carboxyl group; exocyclic double bond; furan; secochiliolide acid derivative; spironolactone; unclassified drug; article; drug activity; drug bioavailability; drug synthesis; epimastigote; epoxidation; high performance liquid chromatography; IC 50; medicinal plant; Nardophyllum bryoides; nonhuman; shrub; Trypanosoma cruzi; Nardophyllum bryoides; Trypanosoma cruzi; Nardophyllum bryoides; Secochiliolide acid; trypanocidal activity; Trypanosoma cruzi; Asteraceae; Chagas Disease; Diterpenes; Humans; Propionates; Trypanocidal Agents; Trypanosoma cruzi |
| Año: | 2013 |
| Volumen: | 23 |
| Número: | 17 |
| Página de inicio: | 4964 |
| Página de fin: | 4967 |
| DOI: | http://dx.doi.org/10.1016/j.bmcl.2013.06.064 |
| Título revista: | Bioorganic and Medicinal Chemistry Letters |
| Título revista abreviado: | Bioorg. Med. Chem. Lett. |
| ISSN: | 0960894X |
| CODEN: | BMCLE |
| CAS: | benznidazole, 22994-85-0; furan, 110-00-9; spironolactone, 52-01-7 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0960894X_v23_n17_p4964_Siless |
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Citas:
---------- APA ----------
Siless, G.E., Lozano, E., Sánchez, M., Mazzuca, M., Sosa, M.A. & Palermo, J.A. (2013) . Preparation and antitrypanosomal activity of secochiliolide acid derivatives. Bioorganic and Medicinal Chemistry Letters, 23(17), 4964-4967.http://dx.doi.org/10.1016/j.bmcl.2013.06.064
---------- CHICAGO ----------
Siless, G.E., Lozano, E., Sánchez, M., Mazzuca, M., Sosa, M.A., Palermo, J.A. "Preparation and antitrypanosomal activity of secochiliolide acid derivatives" . Bioorganic and Medicinal Chemistry Letters 23, no. 17 (2013) : 4964-4967.http://dx.doi.org/10.1016/j.bmcl.2013.06.064
---------- MLA ----------
Siless, G.E., Lozano, E., Sánchez, M., Mazzuca, M., Sosa, M.A., Palermo, J.A. "Preparation and antitrypanosomal activity of secochiliolide acid derivatives" . Bioorganic and Medicinal Chemistry Letters, vol. 23, no. 17, 2013, pp. 4964-4967.http://dx.doi.org/10.1016/j.bmcl.2013.06.064
---------- VANCOUVER ----------
Siless, G.E., Lozano, E., Sánchez, M., Mazzuca, M., Sosa, M.A., Palermo, J.A. Preparation and antitrypanosomal activity of secochiliolide acid derivatives. Bioorg. Med. Chem. Lett. 2013;23(17):4964-4967.http://dx.doi.org/10.1016/j.bmcl.2013.06.064
