Synthesis and Evaluation of the Cytotoxicity of Apoptolidinones A and D

[Image: see text] Apoptolidins A−D are microbial secondary metabolites shown to be selectively cytotoxic against several cancer cell lines and noncytotoxic against normal cells. Total syntheses of apoptolidinones A and D are reported. The efficient synthetic strategy leading to the apoptolidinones f...

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Autores principales: Ghidu, Victor P., Wang, Jingqi, Wu, Bin, Liu, Qingsong, Jacobs, Aaron, Marnett, Lawrence J., Sulikowski, Gary A.
Formato: Texto
Lenguaje:English
Publicado: American Chemical Society 2008
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2572754/
https://www.ncbi.nlm.nih.gov/pubmed/18543990
http://dx.doi.org/10.1021/jo800545r
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author Ghidu, Victor P.
Wang, Jingqi
Wu, Bin
Liu, Qingsong
Jacobs, Aaron
Marnett, Lawrence J.
Sulikowski, Gary A.
author_facet Ghidu, Victor P.
Wang, Jingqi
Wu, Bin
Liu, Qingsong
Jacobs, Aaron
Marnett, Lawrence J.
Sulikowski, Gary A.
author_sort Ghidu, Victor P.
collection PubMed
description [Image: see text] Apoptolidins A−D are microbial secondary metabolites shown to be selectively cytotoxic against several cancer cell lines and noncytotoxic against normal cells. Total syntheses of apoptolidinones A and D are reported. The efficient synthetic strategy leading to the apoptolidinones features construction of the common 20-membered macrolactone by an intramolecular Suzuki reaction and stereocontrolled aldol reactions establishing the C19/C20 and C22/C23 stereocenters. In contrast to apoptolidin A, the aglycones apoptolidinone A and D were shown to be noncytotoxic when evaluated against human lung cancer cells (H292).
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spelling pubmed-25727542009-03-20 Synthesis and Evaluation of the Cytotoxicity of Apoptolidinones A and D Ghidu, Victor P. Wang, Jingqi Wu, Bin Liu, Qingsong Jacobs, Aaron Marnett, Lawrence J. Sulikowski, Gary A. J Org Chem [Image: see text] Apoptolidins A−D are microbial secondary metabolites shown to be selectively cytotoxic against several cancer cell lines and noncytotoxic against normal cells. Total syntheses of apoptolidinones A and D are reported. The efficient synthetic strategy leading to the apoptolidinones features construction of the common 20-membered macrolactone by an intramolecular Suzuki reaction and stereocontrolled aldol reactions establishing the C19/C20 and C22/C23 stereocenters. In contrast to apoptolidin A, the aglycones apoptolidinone A and D were shown to be noncytotoxic when evaluated against human lung cancer cells (H292). American Chemical Society 2008-06-11 2008-07-04 /pmc/articles/PMC2572754/ /pubmed/18543990 http://dx.doi.org/10.1021/jo800545r Text en Copyright © 2008 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org. 40.75
spellingShingle Ghidu, Victor P.
Wang, Jingqi
Wu, Bin
Liu, Qingsong
Jacobs, Aaron
Marnett, Lawrence J.
Sulikowski, Gary A.
Synthesis and Evaluation of the Cytotoxicity of Apoptolidinones A and D
title Synthesis and Evaluation of the Cytotoxicity of Apoptolidinones A and D
title_full Synthesis and Evaluation of the Cytotoxicity of Apoptolidinones A and D
title_fullStr Synthesis and Evaluation of the Cytotoxicity of Apoptolidinones A and D
title_full_unstemmed Synthesis and Evaluation of the Cytotoxicity of Apoptolidinones A and D
title_short Synthesis and Evaluation of the Cytotoxicity of Apoptolidinones A and D
title_sort synthesis and evaluation of the cytotoxicity of apoptolidinones a and d
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2572754/
https://www.ncbi.nlm.nih.gov/pubmed/18543990
http://dx.doi.org/10.1021/jo800545r
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