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 GE; UMYMFOR-Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina., Knott ME, Derita MG, Zacchino SA, Puricelli L, Palermo JA |
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| Jazyk: | angličtina |
| Zdroj: | Steroids [Steroids] 2012 Jan; Vol. 77 (1-2), pp. 45-51. Date of Electronic Publication: 2011 Oct 06. |
| DOI: | 10.1016/j.steroids.2011.09.012 |
| Abstrakt: | 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. (Copyright © 2011 Elsevier Inc. All rights reserved.) |
| Databáze: | MEDLINE |
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