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Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds
dc.creator | Milić, Dragana | |
dc.creator | Kop, Tatjana | |
dc.creator | Juranić, Z. | |
dc.creator | Gasic, MJ | |
dc.creator | Tinant, B | |
dc.creator | Pocsfalvi, G | |
dc.creator | Šolaja, Bogdan A. | |
dc.date.accessioned | 2018-11-22T00:09:02Z | |
dc.date.available | 2018-11-22T00:09:02Z | |
dc.date.issued | 2005 | |
dc.identifier.issn | 0039-128X | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/748 | |
dc.description.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. | en |
dc.publisher | Elsevier Science Inc, New York | |
dc.rights | restrictedAccess | |
dc.source | Steroids | |
dc.subject | aromatization | en |
dc.subject | conduritol | en |
dc.subject | rearrangement | en |
dc.subject | anticancer activity | en |
dc.title | Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Коп, Т; Милић, Драгана; Поцсфалви, Г; Тинант, Б; Гасиц, МЈ; Јураниц, З; Шолаја, Богдан A.; | |
dc.citation.volume | 70 | |
dc.citation.issue | 14 | |
dc.citation.spage | 922 | |
dc.citation.epage | 932 | |
dc.identifier.wos | 000234549400002 | |
dc.identifier.doi | 10.1016/j.steroids.2005.07.001 | |
dc.citation.other | 70(14): 922-932 | |
dc.citation.rank | M22 | |
dc.identifier.pmid | 16139855 | |
dc.type.version | publishedVersion | en |
dc.identifier.scopus | 2-s2.0-27844533964 |