A flexible, direct, high yielding synthesis of 2-alkylsulfanyl estrogens from estrone has been developed. 2-Methylsulfanyl estradiol (2-MeSE2) 7 displays a similar anti-proliferative activity to the established 2-methoxyestradiol (2-MeOE2) 1, whilst its 3-O-sulfamate derivative (2-MeSE2MATE) 9 exhibits greatly enhanced anti-proliferative activity, combined with significant inhibition of steroid sulfatase, an enzyme target for the treatment of hormone-dependent tumours. (C) 2004 Elsevier Ltd. All rights reserved.
Leese, M. P., Newman, S. P., Purohit, A., Reed, M. J., & Potter, B. V. L. (2004). 2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents. Bioorganic & Medicinal Chemistry Letters, 14(12), 3135-3138. https://doi.org/10.1016/j.bmcl.2004.04.027