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

GASTÓN E. SILESS, JORGE A. PALERMO; MARÍA E. KNOTT, LYDIA PURICELLI; MARCOS G. DERITTA, SUSANA A. ZACHINO

STEROIDS

ELSEVIER SCIENCE INC

Año: 2012 vol. 77 p. 45 - 51

0039-128X

Twelve new hydroquinones and quinones (4a-c ? 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 preliminary results against PANC1 pancreas solid-tumor cell line, with greater activity than the commercial drug doxorubicin.