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

Solaja, BA;Dermanovic, M;Lim, DM;Paik, YK;Declerq, JP.;et.al.
(1997) Steroids — Vol. 62, n° 11, p. 709-718 (1997)

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Authors
  • Solaja, BA
    Author
  • Dermanovic, M
    Author
  • Lim, DM
    Author
  • Paik, YK
    Author
  • Tinant, BernardUCLouvain
    Author
  • Declerq, JP.
    Author
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Abstract
The synthesis of Delta(7,9(11))-lanostadiene derivatives functionalized at C(32) starting from 3 beta-acetoxy-7 alpha,32-epoxylanostan-11-one has been presented. The Delta(7,9(11)) moiety was efficiently introduced in three steps in 71% yield by the regioselective abstraction of allylic 8 beta hydrogen. The formyl group of the key intermediate, 3 beta-benzoyloxylanosta-7,9(11)-dien-32-al, has been stereoselectively alkylated into (32S) derivative, whereas its oxidation unexpectedly afforded 3 beta-benxoyloxy-7-oxolanost-8-ene-32,11 alpha-lactone and not the corresponding acid. Delta(7,9(11))-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 mu M. (C) 1997 by Elsevier Science, Inc.
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Solaja, B., Dermanovic, M., Lim, D., Paik, Y., Tinant, B., & Declerq, JP. (1997). The synthesis and in vitro activity of some Delta(7,9(11))-lanostadienes. Steroids, 62(11), 709-718. https://doi.org/10.1016/S0039-128X(97)00075-5 (Original work published 1997)