Estrone derived steroidal diepoxide: biologically active compound and precursor of a stable steroidal A,B-spiro system.
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.
Milic
Dragana
D
Faculty of Chemistry University of Belgrade, Studentski trg 12-16, POB 51, 11158 Belgrade, Serbia. dmilic@chem.bg.ac.rs
Kop
Tatjana
T
Csanadi
Janos
J
Juranic
Zorica
Z
Zizak
Zeljko
Z
Gasic
Miroslav J
MJ
Solaja
Bogdan
B
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004852:Epoxy Compounds / Q000737:chemistry*; D004970:Estrone / Q000031:analogs & derivatives*; D006801:Humans; D008698:Mesylates / Q000737:chemistry; D051379:Mice; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D014297:Trimethylsilyl Compounds / Q000737:chemistry; D023041:Xenograft Model Antitumor Assays
D000970:Antineoplastic Agents; D004852:Epoxy Compounds; D008698:Mesylates; D013141:Spiro Compounds; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; D004970:Estrone