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...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Li, Li, Zheng-Wei, Zhang, Wei, Xu, Rui, Gao, Fei, Liu, Yang-Feng, Li, Ya-Jun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
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
_version_ 1783376835798630400
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
work_keys_str_mv AT wangli synthesiscrystalstructureandbiologicalevaluationofaseriesofphloretinderivatives
AT lizhengwei synthesiscrystalstructureandbiologicalevaluationofaseriesofphloretinderivatives
AT zhangwei synthesiscrystalstructureandbiologicalevaluationofaseriesofphloretinderivatives
AT xurui synthesiscrystalstructureandbiologicalevaluationofaseriesofphloretinderivatives
AT gaofei synthesiscrystalstructureandbiologicalevaluationofaseriesofphloretinderivatives
AT liuyangfeng synthesiscrystalstructureandbiologicalevaluationofaseriesofphloretinderivatives
AT liyajun synthesiscrystalstructureandbiologicalevaluationofaseriesofphloretinderivatives