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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 \u00b1 0.07 \u03bcM for ER\u03b1 and a selectivity of 12.8-fold toward ER\u03b2. 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