6-(2-adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate: a potent non-steroidal irreversible inhibitor of human steroid sulfatase

EP Schreiner, B Wolff, AP Winiski, A Billich

Index: Schreiner, Erwin P.; Wolff, Barbara; Winiski, Anthony P.; Billich, Andreas Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 24 p. 4313 - 4316

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Citation Number: 26

Abstract

We report the synthesis and results from the in vitro evaluation of 6-(adamantan-2-ylidene- hydroxybenzoxazole)-O-sulfamate 1 as an irreversible inhibitor of human steroid sulfatase (STS). Highly straightforward, condensation of 2-methyl-6-hydroxybenzoxazole with 2- adamantanone, subsequent elimination of water and sulfamoylation provide the title compound in 45% overall yield from the inexpensive 2, 4-dihydroxyacetophenone. 1 was ...

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