The synthesis and in vitro activity of some Delta(7,9(11))-lanostadienes
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.
Keywords:
Delta(7,9(11))lanostadienes / synthesis / inhibitory activity / cholesterogenic enzymes / X-ray analysisSource:
Steroids, 1997, 62, 11, 709-718Publisher:
- Elsevier Science Inc, New York
DOI: 10.1016/S0039-128X(97)00075-5
ISSN: 0039-128X
PubMed: 9366010
WoS: A1997YF63700005
Scopus: 2-s2.0-0030707748
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - 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 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" }
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
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 .
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 . .