Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds
Само за регистроване кориснике
2005
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
aromatization / conduritol / rearrangement / anticancer activityИзвор:
Steroids, 2005, 70, 14, 922-932Издавач:
- 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
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - 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 . .