Structure-activity relationships of C-17-substituted estratriene-3-O-sulfamates as anticancer agents

Fabrice Jourdan, Mathew P. Leese, Wolfgang Dohle, Eric Ferrandis, Simon P. Newman, Surinder Chander, Atul Purohit, Barry V. L. Potter

Research output: Contribution to journalArticlepeer-review

18 Citations (SciVal)


The synthesis and antiproliferative activities of analogues of 2-substituted estradiol-3,17-O,O-bis-sulfamates (E2bisMATEs) are discussed. Modifications of the C-17 substituent confirm that an H-bond acceptor is essential for high activity; its optimal linkage to C-17 and the local environment in which it resides are defined. In the non-sulfamoylated series 17 beta-acyl substitution delivers 48b, the most potent compound identified to date. In the sulfamate series a number of permutations of linker and H-bond acceptor deliver excellent activity, with 55, 61, 65, 49a, and 49b proving especially promising. The in vivo potential of these compounds was explored in the NCI hollow fiber assay and also in a mouse Matrigel model of antiangiogenesis in which 49 and 55 show significant inhibitory activity.
Original languageEnglish
Pages (from-to)4863-4879
JournalJournal of Medicinal Chemistry
Issue number13
Early online date22 May 2011
Publication statusPublished - 14 Jul 2011


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