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Medicinal Chemistry

Author(s): Zhifang Yang, Yi Liu, Zhuo Liu, Qinfang Xu, Shun Liu, Kailin Jiang, Yuanlong Shi, Wenyu Xu, Zehua Yang, Pengbing Mi, Yijun Xiang*, Xu Yao* and Xing Zheng*

DOI: 10.2174/1573406418666220607140651

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Design, Synthesis, and Anti-Breast Cancer Activity of Novel Fluorinated 7-O-Modified Genistein Derivatives

Page: [64 - 74] Pages: 11

  • * (Excluding Mailing and Handling)

Abstract

Background: Genistein has been limited in clinical application due to its low bioavailability, extremely poor liposolubility, and fast glycosylation rate, though it possesses anti-breast cancer activity. Therefore, the discovery of novel genistein derivatives is an urgency.

Objective: To enhance the anti-breast cancer activity of genistein, a series of novel fluorinated genistein derivatives were synthesized.

Methods: Their in vitro antitumor activity was investigated by the MTT assay against three cancer cell lines, via, MDA-MB-231, MCF-7, and MDA-MB-435, respectively.

Results: Analogs 1d, 2b, and 3b showed remarkable anticancer activities compared to tamoxifen, a clinical anti-breast cancer drug on the market.

Conclusion: The activities against breast cancer of genistein were enhanced by introducing the 7- alkoxyl group and fluorine atom into the B-ring. Therefore, these compounds may be potential candidates for treating breast cancer.

Keywords: Anti-breast cancer activities, Genistein, Baker-Venkataraman reaction, Fluorinated-genistein derivatives, MTT assay, structure-activity relationship

Graphical Abstract

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