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

doi:10.1134/S1068162010060117

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

Not published at Aalto University

Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
RAS - Institute of Biomedical Chemistry
RAS - Engelhardt Institute of Molecular Biology

Research output: Contribution to journal › Article › Scientific › peer-review

12 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 language	English
Pages (from-to)	746-754
Number of pages	9
Journal	Russian Journal of Bioorganic Chemistry
Volume	36
Issue number	6
DOIs	https://doi.org/10.1134/S1068162010060117
Publication status	Published - 1 Nov 2010
MoE publication type	A1 Journal article-refereed

Funding

ACKNOWLEDGMENTS The work was supported by the Russian Founda tion for Basic Research (project nos. 08 04 90023 Bel_a and 07 04 01155 a) and the Belarusian Repub lican Foundation for Basic Research (project no. Kh08R 031).

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Brassinolide
Brassinosteroids
Olefination
Secasterol
Sulfones

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10.1134/S1068162010060117

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title = "Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells",

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.",

keywords = "Brassinolide, Brassinosteroids, Olefination, Secasterol, Sulfones",

author = "Khripach, \{V. A.\} and Zhabinskii, \{V. N.\} and Gulyakevich, \{O. V.\} and Konstantinova, \{O. V.\} and Misharin, \{A. Yu\} and Mekhtiev, \{A. R.\} and Timofeev, \{V. P.\} and Tkachev, \{Ya V.\}",

year = "2010",

month = nov,

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doi = "10.1134/S1068162010060117",

language = "English",

volume = "36",

pages = "746--754",

journal = "Russian Journal of Bioorganic Chemistry",

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TY - JOUR

T1 - Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells

AU - Khripach, V. A.

AU - Zhabinskii, V. N.

AU - Gulyakevich, O. V.

AU - Konstantinova, O. V.

AU - Misharin, A. Yu

AU - Mekhtiev, A. R.

AU - Timofeev, V. P.

AU - Tkachev, Ya V.

PY - 2010/11/1

Y1 - 2010/11/1

N2 - 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.

AB - 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.

KW - Brassinolide

KW - Brassinosteroids

KW - Olefination

KW - Secasterol

KW - Sulfones

UR - https://www.scopus.com/pages/publications/78649997663

U2 - 10.1134/S1068162010060117

DO - 10.1134/S1068162010060117

M3 - Article

AN - SCOPUS:78649997663

SN - 1068-1620

VL - 36

SP - 746

EP - 754

JO - Russian Journal of Bioorganic Chemistry

JF - Russian Journal of Bioorganic Chemistry

IS - 6

ER -

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

Abstract

Funding

UN SDGs

Keywords

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