Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system
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2009
Authors
Milić, DraganaKop, Tatjana
Csanadi, Janos
Juranić, Zorica D.
Žižak, Željko S.
Gasic, Miroslav J.
Šolaja, Bogdan A.
Article (Published version)
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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 anti proliferative activity of the spiro-product against three cancer cell lines, are also presented. (C) 2009 Elsevier Inc. All rights reserved.
Keywords:
Anticancer activity / Steroidal epoxide / A,B-spiro / TMSOTf / RearrangementSource:
Steroids, 2009, 74, 12, 890-895Publisher:
- Elsevier Science Inc, New York
Funding / projects:
- Sinteza, karakterizacija i primena novih derivata fulerena (RS-MESTD-MPN2006-2010-142049)
DOI: 10.1016/j.steroids.2009.06.002
ISSN: 0039-128X
PubMed: 19538979
WoS: 000270759500003
Scopus: 2-s2.0-70049110807
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Milić, Dragana AU - Kop, Tatjana AU - Csanadi, Janos AU - Juranić, Zorica D. AU - Žižak, Željko S. AU - Gasic, Miroslav J. AU - Šolaja, Bogdan A. PY - 2009 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1020 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 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 anti proliferative activity of the spiro-product against three cancer cell lines, are also presented. (C) 2009 Elsevier Inc. All rights reserved. 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, Janos and Juranić, Zorica D. and Žižak, Željko S. and Gasic, Miroslav J. and Šolaja, Bogdan A.", 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 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 anti proliferative activity of the spiro-product against three cancer cell lines, are also presented. (C) 2009 Elsevier Inc. All rights reserved.", 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. D., Žižak, Ž. S., Gasic, M. J.,& Šolaja, B. A.. (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 ZD, Žižak ŽS, Gasic MJ, Šolaja BA. 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, Janos, Juranić, Zorica D., Žižak, Željko S., Gasic, Miroslav J., Šolaja, Bogdan A., "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 . .