Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells

V. A. Khripach, V. N. Zhabinskii, O. V. Gulyakevich, O. V. Konstantinova, A. Yu Misharin, A. R. Mekhtiev, V. P. Timofeev, Ya V. Tkachev

Research output: Contribution to journalArticleScientificpeer-review

10 Citations (Scopus)

Abstract

The convergent synthesis of biosynthetic precursors of brassinosteroids with a Δ2-bond in cycle A-secasterol and 24-episecasterol-was performed. The key stages in the construction of the side chain in these compounds were the Julia olefination of the steroid 22-aldehyde followed by the Sharpless asymmetric dihydroxylation of the intermediate Δ22- olefin. The cytotoxicity of the synthesized compounds for breast carcinoma MCF-7 cells was assessed.

Original languageEnglish
Pages (from-to)746-754
Number of pages9
JournalRUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
Volume36
Issue number6
DOIs
Publication statusPublished - 1 Nov 2010
MoE publication typeA1 Journal article-refereed

Keywords

  • Brassinolide
  • Brassinosteroids
  • Olefination
  • Secasterol
  • Sulfones

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