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We recently investigated the relationship between the structures of various indenestrols and their cytotoxicity, and reported that indenestrol A (IA), a metabolite of the synthetic nonsteroidal estrogen diethylstilbestrol, and indenestrol B (IB), an analog of IA, disrupt the microtubule architecture of Chinese hamster V79 cells in vitro. We then synthesized 16 optically active indenestrol derivatives by substituting monoethyl, monobenzyl and diethyl ether groups at the 6- and/or 4'-hydroxyl positions, and examined their cytotoxic activities in Chinese hamster V79 cells. The results indicated that the monoethyl ethers had cytotoxic activities similar to monomethyl ethers. However, the (+)- and (-)-monobenzyl ethers were less cytotoxic than the corresponding monomethyl and monoethyl derivatives.

Effects of the Ethyl and Benzyl Ethers of Indenestrols A and B on Cytotoxicity in Chinese Hamster V79 Cells.