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

Authorized Users Only
2009
Authors
Milić, Dragana
Kop, Tatjana
Csanadi, J.
Juranić, Zorica
Žižak, Željko
Gašić, Miroslav J.
Šolaja, Bogdan
Article (Published version)
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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 Ac2O-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.
Keywords:
A,B-spiro / Anticancer activity / Rearrangement / Steroidal epoxide / TMSOTf
Source:
Steroids, 2009, 74, 12, 890-895
Publisher:
  • Elsevier Science Inc, New York
Funding / projects:
  • Sinteza, karakterizacija i primena novih derivata fulerena (RS-142049)

DOI: 10.1016/j.steroids.2009.06.002

ISSN: 0039-128X

PubMed: 19538979

WoS: 000270759500003

Scopus: 2-s2.0-70049110807
[ Google Scholar ]
8
7
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/618
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Csanadi, J.
AU  - Juranić, Zorica
AU  - Žižak, Željko
AU  - Gašić, Miroslav J.
AU  - Šolaja, Bogdan
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/618
AB  - A simple approach to a stable steroidal estrone derived A,B-spiro system is reported. Treatment of estrone derived A-ring diepoxyalcohol with the Ac2O-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.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system
VL  - 74
IS  - 12
SP  - 890
EP  - 895
DO  - 10.1016/j.steroids.2009.06.002
ER  - 
@article{
author = "Milić, Dragana and Kop, Tatjana and Csanadi, J. and Juranić, Zorica and Žižak, Željko and Gašić, Miroslav J. and Šolaja, Bogdan",
year = "2009",
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 Ac2O-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.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system",
volume = "74",
number = "12",
pages = "890-895",
doi = "10.1016/j.steroids.2009.06.002"
}
Milić, D., Kop, T., Csanadi, J., Juranić, Z., Žižak, Ž., Gašić, M. J.,& Šolaja, B.. (2009). Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system. in Steroids
Elsevier Science Inc, New York., 74(12), 890-895.
https://doi.org/10.1016/j.steroids.2009.06.002
Milić D, Kop T, Csanadi J, Juranić Z, Žižak Ž, Gašić MJ, Šolaja B. Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system. in Steroids. 2009;74(12):890-895.
doi:10.1016/j.steroids.2009.06.002 .
Milić, Dragana, Kop, Tatjana, Csanadi, J., Juranić, Zorica, Žižak, Željko, Gašić, Miroslav J., Šolaja, Bogdan, "Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system" in Steroids, 74, no. 12 (2009):890-895,
https://doi.org/10.1016/j.steroids.2009.06.002 . .

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