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.
TY - JOUR
AU - Šolaja, Bogdan A.
AU - Dermanovic, M
AU - Lim, DM
AU - Paik, YK
AU - Tinant, B
AU - Declerq, JP
PY - 1997
UR - https://cherry.chem.bg.ac.rs/handle/123456789/2600
AB - 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.
PB - Elsevier Science Inc, New York
T2 - Steroids
T1 - The synthesis and in vitro activity of some Delta(7,9(11))-lanostadienes
VL - 62
IS - 11
SP - 709
EP - 718
DO - 10.1016/S0039-128X(97)00075-5
UR - Kon_3603
ER -
@article{
author = "Šolaja, Bogdan A. and Dermanovic, M and Lim, DM and Paik, YK and Tinant, B and Declerq, JP",
year = "1997",
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.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "The synthesis and in vitro activity of some Delta(7,9(11))-lanostadienes",
volume = "62",
number = "11",
pages = "709-718",
doi = "10.1016/S0039-128X(97)00075-5",
url = "Kon_3603"
}
Šolaja, B. A., Dermanovic, M., Lim, D., Paik, Y., Tinant, B.,& Declerq, J.. (1997). The synthesis and in vitro activity of some Delta(7,9(11))-lanostadienes. in Steroids
Elsevier Science Inc, New York., 62(11), 709-718.
https://doi.org/10.1016/S0039-128X(97)00075-5
Kon_3603
Šolaja BA, Dermanovic M, Lim D, Paik Y, Tinant B, Declerq J. The synthesis and in vitro activity of some Delta(7,9(11))-lanostadienes. in Steroids. 1997;62(11):709-718.
doi:10.1016/S0039-128X(97)00075-5
Kon_3603 .
Šolaja, Bogdan A., Dermanovic, M, Lim, DM, Paik, YK, Tinant, B, Declerq, JP, "The synthesis and in vitro activity of some Delta(7,9(11))-lanostadienes" in Steroids, 62, no. 11 (1997):709-718,
https://doi.org/10.1016/S0039-128X(97)00075-5 .,
Kon_3603 .
