Synthesis of Carborane-Containing Flavone and Flavonol Analogues as ER Agonists and COX Inhibitors

IF 3.7 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-08-19 DOI:10.1021/acs.jnatprod.5c01639

Yirong Zhang, Chenyang Ma, Lili Wang, Yuan Li, Yuzhe Lin, Zekun Yang, Changxian Yuan, Guanxiang Hao, Linyuan Wang, Hongjing Li, Nan Sun, Zhangxiang Yin, Yong Nian, Sinan Wang, Mary Beth

引用次数: 0

Abstract

Flavones and flavonols are natural products and privileged structures with diverse bioactivities. Carboranes are considered three-dimensional bioisosteric surrogate for phenyl rings. Herein, the terminal phenyl group of flavones and flavonols was replaced with carborane and a series of carborane-containing flavone and flavonol analogues were successfully prepared. These compounds exhibited estrogen receptor (ER) agonist activities. Compound 1 showed an EC₅₀ of 0.87 ± 0.07 μM for ERα and a selectivity of 12.8-fold toward ERβ. These compounds also showed moderate inhibitory activities towards COX-1 and COX-2.

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含碳硼烷黄酮和黄酮醇类似物作为内质网激动剂和COX抑制剂的合成。

黄酮和黄酮醇是具有多种生物活性的天然产物和特殊结构。碳硼烷被认为是苯环的三维生物等构替代物。本文将黄酮和黄酮醇的末端苯基替换为碳硼烷，成功制备了一系列含碳硼烷的黄酮和黄酮醇类似物。这些化合物具有雌激素受体（ER）激动剂活性。化合物1对ERα的EC50为0.87±0.07 μM，对ERβ的选择性为12.8倍。这些化合物对COX-1和COX-2也有一定的抑制作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.