Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds
| Autor: | Milic D., Kop T., Juranic Z., Gasic M. J., Tinant B., Pocsfalvi G., Solaja B. A. |
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| Jazyk: | angličtina |
| Rok vydání: | 2005 |
| Zdroj: | Steroids 70 (2005): 922–932. info:cnr-pdr/source/autori:Milic D., Kop T., Juranic Z., Gasic M. J., Tinant B., Pocsfalvi G., Solaja B. A./titolo:Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds./doi:/rivista:Steroids/anno:2005/pagina_da:922/pagina_a:932/intervallo_pagine:922–932/volume:70 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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