Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes

Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone...

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Autores principales: Catalán, Luis Espinoza, Maturana, Evelyn Baeza, Marín, Karen Catalán, Olivares, Mauricio Osorio, Altamirano, Héctor Carrasco, Fritis, Mauricio Cuellar, García, Joan Villena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257776/
https://www.ncbi.nlm.nih.gov/pubmed/20877240
http://dx.doi.org/10.3390/molecules15096502
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author Catalán, Luis Espinoza
Maturana, Evelyn Baeza
Marín, Karen Catalán
Olivares, Mauricio Osorio
Altamirano, Héctor Carrasco
Fritis, Mauricio Cuellar
García, Joan Villena
author_facet Catalán, Luis Espinoza
Maturana, Evelyn Baeza
Marín, Karen Catalán
Olivares, Mauricio Osorio
Altamirano, Héctor Carrasco
Fritis, Mauricio Cuellar
García, Joan Villena
author_sort Catalán, Luis Espinoza
collection PubMed
description Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF(3)(.)Et(2)O as a catalyst. These compounds, along with a series of natural ent-labdanes 3-8, have been evaluated for their in vitro cytotoxic activities against cultured human cancer cells of PC-3 and DU-145 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma and dermal human fibroblasts (DHF). Some compounds displayed inhibition at µM IC(50 )values.
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spelling pubmed-62577762018-12-06 Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes Catalán, Luis Espinoza Maturana, Evelyn Baeza Marín, Karen Catalán Olivares, Mauricio Osorio Altamirano, Héctor Carrasco Fritis, Mauricio Cuellar García, Joan Villena Molecules Article Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF(3)(.)Et(2)O as a catalyst. These compounds, along with a series of natural ent-labdanes 3-8, have been evaluated for their in vitro cytotoxic activities against cultured human cancer cells of PC-3 and DU-145 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma and dermal human fibroblasts (DHF). Some compounds displayed inhibition at µM IC(50 )values. MDPI 2010-09-17 /pmc/articles/PMC6257776/ /pubmed/20877240 http://dx.doi.org/10.3390/molecules15096502 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Catalán, Luis Espinoza
Maturana, Evelyn Baeza
Marín, Karen Catalán
Olivares, Mauricio Osorio
Altamirano, Héctor Carrasco
Fritis, Mauricio Cuellar
García, Joan Villena
Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
title Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
title_full Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
title_fullStr Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
title_full_unstemmed Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
title_short Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
title_sort synthesis and antitumor activity of diterpenylhydroquinone derivatives of natural ent-labdanes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257776/
https://www.ncbi.nlm.nih.gov/pubmed/20877240
http://dx.doi.org/10.3390/molecules15096502
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