Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. (Articolo in rivista)

Type
Label
  • Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. (Articolo in rivista) (literal)
Anno
  • 2005-01-01T00:00:00+01:00 (literal)
Alternative label
  • Milic D., Kop T., Juranic Z., Gasic M. J., Tinant B., Pocsfalvi G., Solaja B. A. (2005)
    Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds.
    in Steroids
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Milic D., Kop T., Juranic Z., Gasic M. J., Tinant B., Pocsfalvi G., Solaja B. A. (literal)
Pagina inizio
  • 922 (literal)
Pagina fine
  • 932 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#altreInformazioni
  • 1 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 70 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Univ Belgrade, Fac Chem, Belgrade 11000, Serbia Monteneg; Inst Oncol & Radiol Serbia, Belgrade 11000, Serbia Monteneg; Dept Chim, Unite CSTR, B-1348 Louvain, Belgium; CNR, Ist Sci Alimentaz, Ctr Spettrometria Massa Proteom & Biomol, Avellino, Italy (literal)
Titolo
  • Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. (literal)
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. (literal)
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