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Abstract:

Twelve new hydroquinones and quinones (4a-c to 7a-c) derived from free or peracetylated bile acids were prepared by a Barton decarboxylation reaction, with subsequent trapping of the resulting free radical by benzoquinone. All new compounds were completely characterized by 2D NMR techniques and screened for antifungal and cytotoxic activity. One of the new hydroquinones (7b) showed promising results against the human pancreatic ductal carcinoma cell line PANC1, with similar cytotoxic activity as the commercial chemotherapy drug doxorubicin. © 2011 Elsevier Inc. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities
Autor:Siless, G.E.; Knott, M.E.; Derita, M.G.; Zacchino, S.A.; Puricelli, L.; Palermo, J.A.
Filiación:UMYMFOR - Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, (1428) Buenos Aires, Argentina
Research Area, Angel H. Roffo Institute of Oncology, University of Buenos Aires, Av. San Martín 5481, (C1417DTB), Buenos Aires, Argentina
Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000)-Rosario, Argentina
Palabras clave:Barton decarboxylation; Benzoquinone; Bile acids; Cytotoxic activity; Quinones; 23 hydroquinoyl 3alpha hydroxy 24 nor 5beta cholane; benzoquinone derivative; bile acid; doxorubicin; hydroquinone derivative; quinone derivative; unclassified drug; addition reaction; antifungal activity; article; cancer cell culture; controlled study; decarboxylation; drug cytotoxicity; drug synthesis; human; human cell; nonhuman; pancreas carcinoma; Animals; Antifungal Agents; Antineoplastic Agents; Benzoquinones; Bile Acids and Salts; Candida albicans; Carcinoma, Pancreatic Ductal; Cell Line, Tumor; Cell Survival; Decarboxylation; Doxorubicin; Drug Design; Free Radicals; Humans; Hydroquinones; Magnetic Resonance Spectroscopy; Molecular Structure; Pancreatic Neoplasms; Quinones; Steroids; Structure-Activity Relationship
Año:2012
Volumen:77
Número:1-2
Página de inicio:45
Página de fin:51
DOI: http://dx.doi.org/10.1016/j.steroids.2011.09.012
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:doxorubicin, 23214-92-8, 25316-40-9; Antifungal Agents; Antineoplastic Agents; Benzoquinones; Bile Acids and Salts; Doxorubicin, 23214-92-8; Free Radicals; Hydroquinones; Quinones; Steroids; benzoquinone, 106-51-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v77_n1-2_p45_Siless

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Citas:

---------- APA ----------
Siless, G.E., Knott, M.E., Derita, M.G., Zacchino, S.A., Puricelli, L. & Palermo, J.A. (2012) . Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities. Steroids, 77(1-2), 45-51.
http://dx.doi.org/10.1016/j.steroids.2011.09.012
---------- CHICAGO ----------
Siless, G.E., Knott, M.E., Derita, M.G., Zacchino, S.A., Puricelli, L., Palermo, J.A. "Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities" . Steroids 77, no. 1-2 (2012) : 45-51.
http://dx.doi.org/10.1016/j.steroids.2011.09.012
---------- MLA ----------
Siless, G.E., Knott, M.E., Derita, M.G., Zacchino, S.A., Puricelli, L., Palermo, J.A. "Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities" . Steroids, vol. 77, no. 1-2, 2012, pp. 45-51.
http://dx.doi.org/10.1016/j.steroids.2011.09.012
---------- VANCOUVER ----------
Siless, G.E., Knott, M.E., Derita, M.G., Zacchino, S.A., Puricelli, L., Palermo, J.A. Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities. Steroids. 2012;77(1-2):45-51.
http://dx.doi.org/10.1016/j.steroids.2011.09.012