The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes

Bogdan A. Šolaja; Miodrag Ermanović; Lim Dong-Min; Young Ki Paik; Bernard Tinant; Jean Paul Declerq

doi:10.1016/S0039-128X(97)00075-5

The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes

Bogdan A. Šolaja, Miodrag Ermanović, Lim Dong-Min, Young Ki Paik, Bernard Tinant, Jean Paul Declerq

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

Abstract

The synthesis of Δ(7,9(911))-lanostadiene derivatives functionalized at C(32) starting from 3β-acetoxy-7α,32-epoxylanostan-11-one has been presented. The Δ(7,9(911)) moiety was efficiently introduced in three steps in 71% yield by the regioselective abstraction of allylic 8β hydrogen. The formyl group of the key intermediate, 3β-benzoyloxylanosta-7,9(11)-dien-32- al, has been stereoselectively alkylated into (32S) derivative, whereas its oxidation unexpectedly afforded 3β-benzoyloxy-7-oxolanost-8-ene-32,11α- lactone and not the corresponding acid. δ(7,9(911))-lanostadienes possessing HC(32)=O, C(32)=N, HC(32S)CH₃OH, H₂C(32)OH, as well as some 11-keto lanostenes, were tested in Vitro against several purified cholesterogenic enzymes showing moderate activity, with most the active aldehyde 16 having IC₅₀ = 86 μm.

Original language	English
Pages (from-to)	709-718
Number of pages	10
Journal	Steroids
Volume	62
Issue number	11
DOIs	https://doi.org/10.1016/S0039-128X(97)00075-5
Publication status	Published - 1997 Nov

Bibliographical note

Funding Information:
The authors from Belgrade wish to thank the Yugoslav Research Fund and Research Fund of Serbia for financial support (Grant S.3.02.24.256). This work was also supported in part by a grant from Korea Science and Engineering Foundation (KOSEF) through the Bioproducts Research Center at Yonsei University (to YKP).

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Biology
Endocrinology
Pharmacology
Clinical Biochemistry
Organic Chemistry

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10.1016/S0039-128X(97)00075-5

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title = "The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes",

abstract = "The synthesis of Δ(7,9(911))-lanostadiene derivatives functionalized at C(32) starting from 3β-acetoxy-7α,32-epoxylanostan-11-one has been presented. The Δ(7,9(911)) moiety was efficiently introduced in three steps in 71% yield by the regioselective abstraction of allylic 8β hydrogen. The formyl group of the key intermediate, 3β-benzoyloxylanosta-7,9(11)-dien-32- al, has been stereoselectively alkylated into (32S) derivative, whereas its oxidation unexpectedly afforded 3β-benzoyloxy-7-oxolanost-8-ene-32,11α- lactone and not the corresponding acid. δ(7,9(911))-lanostadienes possessing HC(32)=O, C(32)=N, HC(32S)CH3OH, H2C(32)OH, as well as some 11-keto lanostenes, were tested in Vitro against several purified cholesterogenic enzymes showing moderate activity, with most the active aldehyde 16 having IC50 = 86 μm.",

author = "{\v S}olaja, {Bogdan A.} and Miodrag Ermanovi{\'c} and Lim Dong-Min and Paik, {Young Ki} and Bernard Tinant and Declerq, {Jean Paul}",

note = "Funding Information: The authors from Belgrade wish to thank the Yugoslav Research Fund and Research Fund of Serbia for financial support (Grant S.3.02.24.256). This work was also supported in part by a grant from Korea Science and Engineering Foundation (KOSEF) through the Bioproducts Research Center at Yonsei University (to YKP).",

year = "1997",

month = nov,

doi = "10.1016/S0039-128X(97)00075-5",

language = "English",

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T1 - The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes

AU - Šolaja, Bogdan A.

AU - Ermanović, Miodrag

AU - Dong-Min, Lim

AU - Paik, Young Ki

AU - Tinant, Bernard

AU - Declerq, Jean Paul

N1 - Funding Information: The authors from Belgrade wish to thank the Yugoslav Research Fund and Research Fund of Serbia for financial support (Grant S.3.02.24.256). This work was also supported in part by a grant from Korea Science and Engineering Foundation (KOSEF) through the Bioproducts Research Center at Yonsei University (to YKP).

PY - 1997/11

Y1 - 1997/11

N2 - The synthesis of Δ(7,9(911))-lanostadiene derivatives functionalized at C(32) starting from 3β-acetoxy-7α,32-epoxylanostan-11-one has been presented. The Δ(7,9(911)) moiety was efficiently introduced in three steps in 71% yield by the regioselective abstraction of allylic 8β hydrogen. The formyl group of the key intermediate, 3β-benzoyloxylanosta-7,9(11)-dien-32- al, has been stereoselectively alkylated into (32S) derivative, whereas its oxidation unexpectedly afforded 3β-benzoyloxy-7-oxolanost-8-ene-32,11α- lactone and not the corresponding acid. δ(7,9(911))-lanostadienes possessing HC(32)=O, C(32)=N, HC(32S)CH3OH, H2C(32)OH, as well as some 11-keto lanostenes, were tested in Vitro against several purified cholesterogenic enzymes showing moderate activity, with most the active aldehyde 16 having IC50 = 86 μm.

AB - The synthesis of Δ(7,9(911))-lanostadiene derivatives functionalized at C(32) starting from 3β-acetoxy-7α,32-epoxylanostan-11-one has been presented. The Δ(7,9(911)) moiety was efficiently introduced in three steps in 71% yield by the regioselective abstraction of allylic 8β hydrogen. The formyl group of the key intermediate, 3β-benzoyloxylanosta-7,9(11)-dien-32- al, has been stereoselectively alkylated into (32S) derivative, whereas its oxidation unexpectedly afforded 3β-benzoyloxy-7-oxolanost-8-ene-32,11α- lactone and not the corresponding acid. δ(7,9(911))-lanostadienes possessing HC(32)=O, C(32)=N, HC(32S)CH3OH, H2C(32)OH, as well as some 11-keto lanostenes, were tested in Vitro against several purified cholesterogenic enzymes showing moderate activity, with most the active aldehyde 16 having IC50 = 86 μm.

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The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes

Abstract

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