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(2)O-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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry*
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Antineoplastic Agents / pharmacology*
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Antineoplastic Agents / toxicity
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Dose-Response Relationship, Drug
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Epoxy Compounds / chemistry*
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Estrone / analogs & derivatives*
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Humans
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Mesylates / chemistry
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Mice
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Spiro Compounds / chemical synthesis
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Spiro Compounds / chemistry*
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Spiro Compounds / pharmacology*
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Spiro Compounds / toxicity
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Trimethylsilyl Compounds / chemistry
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Xenograft Model Antitumor Assays
Substances
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Antineoplastic Agents
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Epoxy Compounds
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Mesylates
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Spiro Compounds
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Trimethylsilyl Compounds
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trimethylsilyl trifluoromethanesulfonate
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Estrone