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Zambrano, E.E.; Casas, A.G.; Di Venosa, G.M.; Uriburu, M.L.; Duran, F.J.; Palermo, J.A. "Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone" (2017) Phytochemistry Letters. 21:200-205
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Abstract:

Sixteen derivatives, eight of which are new compounds, were prepared from cycloartenone (1) and cycloartanone (2), and the cytotoxic activity of 14 of these compounds, together with 1 and 2, was evaluated against a panel of four cell lines. Compound 1 was obtained from the epiphyte plant Tillandsia tenuifolia collected at Salta, Argentina. Due to chemoselectivity and regioselectivity problems observed in the reactions of compound 1, this substance was hydrogenated to compound 2. The attempted transformations were focused on ring A of the cited triterpenes with the aim to verify previous structure-activity relationships obtained from related compounds. The cytotoxicity results of the derivatives showed that only the diosphenol 13 displayed significant activity against all the tested cell lines. These results show that an oxidized side chain, for example an ether bridge between the side chain and ring D, is necessary for the cytotoxic activity of cycloartane derivatives. © 2017 Phytochemical Society of Europe

Registro:

Documento: Artículo
Título:Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone
Autor:Zambrano, E.E.; Casas, A.G.; Di Venosa, G.M.; Uriburu, M.L.; Duran, F.J.; Palermo, J.A.
Filiación:Facultad de Ciencias Exactas, Universidad Nacional de Salta (UNSa), Salta, 4400, Argentina
Centro de Investigaciones sobre Porfirinas y Porfirias (CIPYP) CONICET and Hospital de Clínicas José de San Martin, Universidad de Buenos Aires, Córdoba 2351, 1<sup>er</sup> subsuelo, Ciudad de Buenos Aires, Buenos Aires, 1120AAF, Argentina
Universidad de Buenos Aires, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2 – (1428), Buenos Aires, Argentina
CONICET-Universidad de Buenos Aires, Unidad de Microanálisis y Métodos Físicos en Química Orgánica (UMYMFOR), Buenos Aires, Argentina
Palabras clave:Cycloartanes; Cycloartanone; Cytotoxicity; Synthetic derivatives; Tillandsia tenuifolia; 2 amino cycloart 1 en 3 one; 2 chloro cycloart 1 en 3 one; 2 hydroxy cycloart 1 en 3 one; 2,2 dibromo cycloartan 3 one; 2,2 dichloro cycloartan 3 one; 2alpha azido cycloartan 3 one; 2alpha chloro cycloartan 3 one; 2alpha fluor cycloartan 3 one; 2beta fluor cycloartan 3 one; 3 benzoyl cycloart 2 ene; antineoplastic agent; cycloartane derivative; cycloartenone derivative; diosphenol; doxorubicin; triterpene derivative; unclassified drug; animal cell; Article; carbon nuclear magnetic resonance; chemical phenomena; chemoselectivity; chlorination; controlled study; cytotoxicity; cytotoxicity assay; drug isolation; drug synthesis; heteronuclear multiple bond correlation; high performance liquid chromatography; human; human cell; hydrogenation; IC50; keratinocyte cell line; MCF-7 cell line; nonhuman; nuclear Overhauser effect; priority journal; proton nuclear magnetic resonance; regioselectivity; structure activity relation; thin layer chromatography; Tillandsia; Tillandsia tenuifolia
Año:2017
Volumen:21
Página de inicio:200
Página de fin:205
DOI: http://dx.doi.org/10.1016/j.phytol.2017.06.021
Título revista:Phytochemistry Letters
Título revista abreviado:Phytochem. Lett.
ISSN:18743900
CODEN:PLHEB
CAS:doxorubicin, 23214-92-8, 25316-40-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18743900_v21_n_p200_Zambrano

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Citas:

---------- APA ----------
Zambrano, E.E., Casas, A.G., Di Venosa, G.M., Uriburu, M.L., Duran, F.J. & Palermo, J.A. (2017) . Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone. Phytochemistry Letters, 21, 200-205.
http://dx.doi.org/10.1016/j.phytol.2017.06.021
---------- CHICAGO ----------
Zambrano, E.E., Casas, A.G., Di Venosa, G.M., Uriburu, M.L., Duran, F.J., Palermo, J.A. "Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone" . Phytochemistry Letters 21 (2017) : 200-205.
http://dx.doi.org/10.1016/j.phytol.2017.06.021
---------- MLA ----------
Zambrano, E.E., Casas, A.G., Di Venosa, G.M., Uriburu, M.L., Duran, F.J., Palermo, J.A. "Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone" . Phytochemistry Letters, vol. 21, 2017, pp. 200-205.
http://dx.doi.org/10.1016/j.phytol.2017.06.021
---------- VANCOUVER ----------
Zambrano, E.E., Casas, A.G., Di Venosa, G.M., Uriburu, M.L., Duran, F.J., Palermo, J.A. Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone. Phytochem. Lett. 2017;21:200-205.
http://dx.doi.org/10.1016/j.phytol.2017.06.021