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Kanbe, Y. et al.

Kanbe, Kim, Nishimoto, Ohtake, Kato, Tsunenari, Taniguchi, Ohizumi, Kaiho, Morikawa, Jo, Lim, Kim,

Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure-activity relationship.

In order to develop pure antiestrogens, a series of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman and 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman derivatives with sulfoxide containing side chains at the 4-position were designed, synthesized, and evaluated. Among them, compounds 14b and 24b functioned as pure antiestrogens with the ability to downregulate ER, and their in vitro and in vivo antiestrogen activities were similar to those of ICI182,780. In addition, the structure-activity relationship indicated that the (3RS,4RS)-configuration between the 3- and 4-position, the methyl group at the 3-position, the 9-methylene chain between the scaffold and the sulfoxide moiety, and the terminal perfluoroalkyl moiety play an important role in increasing estrogen receptor binding and oral antiestrogen activities.[1]

References

Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure-activity relationship. Kanbe, Y., Kim, M.H., Nishimoto, M., Ohtake, Y., Kato, N., Tsunenari, T., Taniguchi, K., Ohizumi, I., Kaiho, S., Morikawa, K., Jo, J.C., Lim, H.S., Kim, H.Y. Bioorg. Med. Chem. (2006) [Pubmed]

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