title: Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities.
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.
authors: UMYMFOR-Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina.
authors: Gastón E
authors: GE
authors: Siless
authors: María E
authors: ME
authors: Knott
authors: Marcos G
authors: MG
authors: Derita
authors: Susana A
authors: SA
authors: Zacchino
authors: Lydia
authors: L
authors: Puricelli
authors: Jorge A
authors: JA
authors: Palermo
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D016227:Benzoquinones / Q000737:chemistry; D001647:Bile Acids and Salts / Q000737:chemistry*; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D021441:Carcinoma, Pancreatic Ductal; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003653:Decarboxylation; D004317:Doxorubicin / Q000494:pharmacology; D015195:Drug Design; D005609:Free Radicals / Q000737:chemistry; D006801:Humans; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010190:Pancreatic Neoplasms; D011809:Quinones / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D013256:Steroids / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D000970:Antineoplastic Agents; D016227:Benzoquinones; D001647:Bile Acids and Salts; D005609:Free Radicals; D006873:Hydroquinones; D011809:Quinones; D013256:Steroids; C004532:quinone; D004317:Doxorubicin