Steroids 2009-01-01

Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system

Dragana Milic, Tatjana Kop, Janos Csanadi, Zorica Juranic, Zeljko Zizak, Miroslav J. Gasic, Bogdan Solaja, Dragana Milic, Tatjana Kop, Janos Csanadi, Zorica Juranic, Zeljko Zizak, Miroslav J. Gasic, Bogdan Solaja

Index: Steroids 74(12) , 890-5, (2009)

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Abstract

A simple approach to a stable steroidal estrone derived A,B-spiro system is reported. Treatment of estrone derived A-ring diepoxyalcohol with the Ac 2O–TMSOTf system at the ambient temperature led to acetylation, while at the reflux temperature the acid-catalysed rearrangement took place affording the spiro-compound. Results of extensive in vitro and in vivo anticancer tests on the diepoxide, as well as preliminary data on the antiproliferative activity of the spiro-product against three cancer cell lines, are also presented.