Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds
(2005) Steroids — Vol. 70, n° 14, p. 922-932 (2005)
Files
pdfdocument.pdf
Restricted Access - Adobe PDF
- 325.43 KB
Details
- Authors
- 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.
- Affiliations
Citations
Milic, D., Kop, T., Juranic, Z., Gasic, M., Tinant, B., Pocsfalvi, G., & Solaja, B. (2005). Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. Steroids, 70(14), 922-932. https://doi.org/10.1016/j.steroids.2005.07.001 (Original work published 2005)