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Istituto di scienza dell'alimentazione

Torna all'elenco Contributi in rivista anno 2005

Contributo in rivista

Tipo: Articolo in rivista

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

Anno di pubblicazione: 2005

Formato: Elettronico Cartaceo

Autori: Milic D., Kop T., Juranic Z., Gasic M. J., Tinant B., Pocsfalvi G., Solaja B. A.

Affiliazioni autori: 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

Autori CNR:

  • GABRIELLA KATALIN POCSFALVI

Lingua: inglese

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.

Pagine da: 922

Pagine a: 932

Rivista:

Steroids Butterworth-Heinemann [etc.]
Paese di pubblicazione: Stati Uniti d'America
Lingua: inglese
ISSN: 0039-128X

Numero volume: 70

Indicizzato da: ISI Web of Science (WOS) [000234549400002]

Altre informazioni: 1

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