Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition: Studies on their cytotoxic and antifungal activities

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.

Palabras clave: BARTON DECARBOXYLATION , BENZOQUINONE , BILE ACIDS , CYTOTOXIC ACTIVITY , QUINONES

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Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)

Identificadores

URI: http://hdl.handle.net/11336/85159

URL: https://www.sciencedirect.com/science/article/pii/S0039128X11003011

DOI: https://doi.org/10.1016/j.steroids.2011.09.012

Colecciones

Articulos(UMYMFOR)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)

Citación

Siless, Gastón Ezequiel; Knott, María Elena; Derita, Marcos Gabriel; Zacchino, Susana Alicia Stella; Puricelli, Lydia Ines; et al.; Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition: Studies on their cytotoxic and antifungal activities; Elsevier Science Inc; Steroids; 77; 1-2; 1-2012; 45-51

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