Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives
A one-step synthesis of phloretin derivatives 2–11 from phloretin in good to excellent yields is reported. Their structures were characterized by (1)H-NMR, (13)C-NMR and MS, and the structures of 8 and 11 were determined by X-ray diffraction analysis. A mechanism for the formation of 9–11 is propose...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271035/ https://www.ncbi.nlm.nih.gov/pubmed/25314605 http://dx.doi.org/10.3390/molecules191016447 |
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author | Wang, Li Li, Zheng-Wei Zhang, Wei Xu, Rui Gao, Fei Liu, Yang-Feng Li, Ya-Jun |
author_facet | Wang, Li Li, Zheng-Wei Zhang, Wei Xu, Rui Gao, Fei Liu, Yang-Feng Li, Ya-Jun |
author_sort | Wang, Li |
collection | PubMed |
description | A one-step synthesis of phloretin derivatives 2–11 from phloretin in good to excellent yields is reported. Their structures were characterized by (1)H-NMR, (13)C-NMR and MS, and the structures of 8 and 11 were determined by X-ray diffraction analysis. A mechanism for the formation of 9–11 is proposed. Compared with the anticancer drug docetaxel, phloretin, phloretin derivatives and phlorizin exhibited moderate cytotoxicity toward the MDA-MB-231, SPC-A1, A549, MCF-7 and EC109 cell lines. Among all of the tested compounds, 7 exhibited the strongest cytotoxicity toward the five cell lines and was more active than docetaxel in MDA-MB-231 cells. Our findings suggest that these derivatives hold great promise for further development as anticancer agents. |
format | Online Article Text |
id | pubmed-6271035 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62710352018-12-27 Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives Wang, Li Li, Zheng-Wei Zhang, Wei Xu, Rui Gao, Fei Liu, Yang-Feng Li, Ya-Jun Molecules Article A one-step synthesis of phloretin derivatives 2–11 from phloretin in good to excellent yields is reported. Their structures were characterized by (1)H-NMR, (13)C-NMR and MS, and the structures of 8 and 11 were determined by X-ray diffraction analysis. A mechanism for the formation of 9–11 is proposed. Compared with the anticancer drug docetaxel, phloretin, phloretin derivatives and phlorizin exhibited moderate cytotoxicity toward the MDA-MB-231, SPC-A1, A549, MCF-7 and EC109 cell lines. Among all of the tested compounds, 7 exhibited the strongest cytotoxicity toward the five cell lines and was more active than docetaxel in MDA-MB-231 cells. Our findings suggest that these derivatives hold great promise for further development as anticancer agents. MDPI 2014-10-13 /pmc/articles/PMC6271035/ /pubmed/25314605 http://dx.doi.org/10.3390/molecules191016447 Text en © 2014 by the authors. 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/4.0/). |
spellingShingle | Article Wang, Li Li, Zheng-Wei Zhang, Wei Xu, Rui Gao, Fei Liu, Yang-Feng Li, Ya-Jun Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives |
title | Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives |
title_full | Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives |
title_fullStr | Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives |
title_full_unstemmed | Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives |
title_short | Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives |
title_sort | synthesis, crystal structure, and biological evaluation of a series of phloretin derivatives |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271035/ https://www.ncbi.nlm.nih.gov/pubmed/25314605 http://dx.doi.org/10.3390/molecules191016447 |
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