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 scre...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Siless, Gastón Ezequiel, Knott, María Elena, Puricelli, Lydia Inés, Palermo, Jorge Alejandro
Publicado:	2012
Materias:	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 Steroids Structure-Activity Relationship
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v77_n1-2_p45_Siless http://hdl.handle.net/20.500.12110/paper_0039128X_v77_n1-2_p45_Siless
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_0039128X_v77_n1-2_p45_Siless
record_format	dspace
spelling	paper:paper_0039128X_v77_n1-2_p45_Siless2023-06-08T15:03:21Z Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities Siless, Gastón Ezequiel Knott, María Elena Puricelli, Lydia Inés Palermo, Jorge Alejandro 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 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. Fil:Siless, G.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Knott, M.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Puricelli, L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Palermo, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2012 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v77_n1-2_p45_Siless http://hdl.handle.net/20.500.12110/paper_0039128X_v77_n1-2_p45_Siless
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Siless, Gastón Ezequiel Knott, María Elena Puricelli, Lydia Inés Palermo, Jorge Alejandro Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities
topic_facet	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
description	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.
author	Siless, Gastón Ezequiel Knott, María Elena Puricelli, Lydia Inés Palermo, Jorge Alejandro
author_facet	Siless, Gastón Ezequiel Knott, María Elena Puricelli, Lydia Inés Palermo, Jorge Alejandro
author_sort	Siless, Gastón Ezequiel
title	Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities
title_short	Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities
title_full	Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities
title_fullStr	Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities
title_full_unstemmed	Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities
title_sort	synthesis of steroidal quinones and hydroquinones from bile acids by barton radical decarboxylation and benzoquinone addition. studies on their cytotoxic and antifungal activities
publishDate	2012
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v77_n1-2_p45_Siless http://hdl.handle.net/20.500.12110/paper_0039128X_v77_n1-2_p45_Siless
work_keys_str_mv	AT silessgastonezequiel synthesisofsteroidalquinonesandhydroquinonesfrombileacidsbybartonradicaldecarboxylationandbenzoquinoneadditionstudiesontheircytotoxicandantifungalactivities AT knottmariaelena synthesisofsteroidalquinonesandhydroquinonesfrombileacidsbybartonradicaldecarboxylationandbenzoquinoneadditionstudiesontheircytotoxicandantifungalactivities AT puricellilydiaines synthesisofsteroidalquinonesandhydroquinonesfrombileacidsbybartonradicaldecarboxylationandbenzoquinoneadditionstudiesontheircytotoxicandantifungalactivities AT palermojorgealejandro synthesisofsteroidalquinonesandhydroquinonesfrombileacidsbybartonradicaldecarboxylationandbenzoquinoneadditionstudiesontheircytotoxicandantifungalactivities
_version_	1768545135266627584

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

Ejemplares similares