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Synthesis, crystal structure, and biological evaluation of a series of phloretin derivatives.

ABSTRACT: A one-step synthesis of phloretin derivatives 2-11 from phloretin in good to excellent yields is reported. Their structures were characterized by 1H-NMR, 13C-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.

SUBMITTER: Wang L

PROVIDER: S-EPMC6271035 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Synthesis, crystal structure, and biological evaluation of a series of phloretin derivatives.

Wang Li L Li Zheng-Wei ZW Zhang Wei W Xu Rui R Gao Fei F Liu Yang-Feng YF Li Ya-Jun YJ

Molecules (Basel, Switzerland) 20141013 10

A one-step synthesis of phloretin derivatives 2-11 from phloretin in good to excellent yields is reported. Their structures were characterized by 1H-NMR, 13C-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 ...[more]

PMID: 25314605

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