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Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds

Authorized Users Only
2005
Authors
Milić, Dragana
Kop, Tatjana
Juranić, Z.
Gasic, MJ
Tinant, B
Pocsfalvi, G
Šolaja, Bogdan A.
Article (Published version)
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Abstract
A simple approach to aromatization of steroidal quinols and epoxyquinols using a catalytic amount of TMSOTf is reported. Beside acetylation of the angular OH, the acid-catalyzed (TfOH) dienone-phenol rearrangement occurred affording "para" products, or in the case of blocked position 4, the acetoxy group 1,2-migration leads to the formation of "meta" products. Using epoxyquinol derivative as a substrate, the acetoxy group elimination was observed, followed by acid-catalyzed epoxy-ring opening and subsequent double bond migration, giving as a final product Delta(9,11) A-ring aromatized compounds. Synthesis of conduritol-like compounds and structure confirmation by X-ray crystallography of the precursor of steroidal conduritol is also described. In addition, the results of extensive antiproliferative screening against a panel of 60 cancer cell lines are presented. (c) 2005 Elsevier Inc. All rights reserved.
Keywords:
aromatization / conduritol / rearrangement / anticancer activity
Source:
Steroids, 2005, 70, 14, 922-932
Publisher:
  • Elsevier Science Inc, New York

DOI: 10.1016/j.steroids.2005.07.001

ISSN: 0039-128X

PubMed: 16139855

WoS: 000234549400002

Scopus: 2-s2.0-27844533964
[ Google Scholar ]
13
11
URI
https://cherry.chem.bg.ac.rs/handle/123456789/748
Collections
  • Publikacije / Publications
Institution/Community
Hemijski fakultet / Faculty of Chemistry
TY  - JOUR
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Juranić, Z.
AU  - Gasic, MJ
AU  - Tinant, B
AU  - Pocsfalvi, G
AU  - Šolaja, Bogdan A.
PY  - 2005
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/748
AB  - A simple approach to aromatization of steroidal quinols and epoxyquinols using a catalytic amount of TMSOTf is reported. Beside acetylation of the angular OH, the acid-catalyzed (TfOH) dienone-phenol rearrangement occurred affording "para" products, or in the case of blocked position 4, the acetoxy group 1,2-migration leads to the formation of "meta" products. Using epoxyquinol derivative as a substrate, the acetoxy group elimination was observed, followed by acid-catalyzed epoxy-ring opening and subsequent double bond migration, giving as a final product Delta(9,11) A-ring aromatized compounds. Synthesis of conduritol-like compounds and structure confirmation by X-ray crystallography of the precursor of steroidal conduritol is also described. In addition, the results of extensive antiproliferative screening against a panel of 60 cancer cell lines are presented. (c) 2005 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds
VL  - 70
IS  - 14
SP  - 922
EP  - 932
DO  - 10.1016/j.steroids.2005.07.001
ER  - 
@article{
author = "Milić, Dragana and Kop, Tatjana and Juranić, Z. and Gasic, MJ and Tinant, B and Pocsfalvi, G and Šolaja, Bogdan A.",
year = "2005",
abstract = "A simple approach to aromatization of steroidal quinols and epoxyquinols using a catalytic amount of TMSOTf is reported. Beside acetylation of the angular OH, the acid-catalyzed (TfOH) dienone-phenol rearrangement occurred affording "para" products, or in the case of blocked position 4, the acetoxy group 1,2-migration leads to the formation of "meta" products. Using epoxyquinol derivative as a substrate, the acetoxy group elimination was observed, followed by acid-catalyzed epoxy-ring opening and subsequent double bond migration, giving as a final product Delta(9,11) A-ring aromatized compounds. Synthesis of conduritol-like compounds and structure confirmation by X-ray crystallography of the precursor of steroidal conduritol is also described. In addition, the results of extensive antiproliferative screening against a panel of 60 cancer cell lines are presented. (c) 2005 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds",
volume = "70",
number = "14",
pages = "922-932",
doi = "10.1016/j.steroids.2005.07.001"
}
Milić, D., Kop, T., Juranić, Z., Gasic, M., Tinant, B., Pocsfalvi, G.,& Šolaja, B. A.. (2005). Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. in Steroids
Elsevier Science Inc, New York., 70(14), 922-932.
https://doi.org/10.1016/j.steroids.2005.07.001
Milić D, Kop T, Juranić Z, Gasic M, Tinant B, Pocsfalvi G, Šolaja BA. Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. in Steroids. 2005;70(14):922-932.
doi:10.1016/j.steroids.2005.07.001 .
Milić, Dragana, Kop, Tatjana, Juranić, Z., Gasic, MJ, Tinant, B, Pocsfalvi, G, Šolaja, Bogdan A., "Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds" in Steroids, 70, no. 14 (2005):922-932,
https://doi.org/10.1016/j.steroids.2005.07.001 . .

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