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 journalArticle

3 Citations (Scopus)

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 languageEnglish
Pages (from-to)709-718
Number of pages10
JournalSteroids
Volume62
Issue number11
DOIs
Publication statusPublished - 1997 Jan 1

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Lactones
Aldehydes
Inhibitory Concentration 50
Hydrogen
Derivatives
Acids
Enzymes
Oxidation
In Vitro Techniques

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Šolaja, B. A., Ermanović, M., Dong-Min, L., Paik, Y-K., Tinant, B., & Declerq, J. P. (1997). The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes. Steroids, 62(11), 709-718. https://doi.org/10.1016/S0039-128X(97)00075-5
Šolaja, Bogdan A. ; Ermanović, Miodrag ; Dong-Min, Lim ; Paik, Young-Ki ; Tinant, Bernard ; Declerq, Jean Paul. / The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes. In: Steroids. 1997 ; Vol. 62, No. 11. pp. 709-718.
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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.",
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Šolaja, BA, Ermanović, M, Dong-Min, L, Paik, Y-K, Tinant, B & Declerq, JP 1997, 'The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes', Steroids, vol. 62, no. 11, pp. 709-718. https://doi.org/10.1016/S0039-128X(97)00075-5

The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes. / Šolaja, Bogdan A.; Ermanović, Miodrag; Dong-Min, Lim; Paik, Young-Ki; Tinant, Bernard; Declerq, Jean Paul.

In: Steroids, Vol. 62, No. 11, 01.01.1997, p. 709-718.

Research output: Contribution to journalArticle

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AU - Šolaja, Bogdan A.

AU - Ermanović, Miodrag

AU - Dong-Min, Lim

AU - Paik, Young-Ki

AU - Tinant, Bernard

AU - Declerq, Jean Paul

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Y1 - 1997/1/1

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.

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Šolaja BA, Ermanović M, Dong-Min L, Paik Y-K, Tinant B, Declerq JP. The synthesis and in vitro activity of some δ(7,9(11))-lanostadienes. Steroids. 1997 Jan 1;62(11):709-718. https://doi.org/10.1016/S0039-128X(97)00075-5