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

Ei julkaistu Aalto-yliopiston affiliaatiolla

Institute of Bioorganic Chemistry of the National Academy of Science of the Republic of Belarus
Russian Academy of Medical Sciences - Institute of Biomedical Chemistry
RAS - Engelhardt Institute of Molecular Biology

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

12 Sitaatiot (Scopus)

Abstrakti

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.

Alkuperäiskieli	Englanti
Sivut	746-754
Sivumäärä	9
Julkaisu	Russian Journal of Bioorganic Chemistry
Vuosikerta	36
Numero	6
DOI - pysyväislinkit	https://doi.org/10.1134/S1068162010060117
Tila	Julkaistu - 1 marrask. 2010
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Rahoitus

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).

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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,

day = "1",

doi = "10.1134/S1068162010060117",

language = "English",

volume = "36",

pages = "746--754",

journal = "Russian Journal of Bioorganic Chemistry",

issn = "1068-1620",

publisher = "MAIK Nauka/Interperiodica",

number = "6",

}

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

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