Impact of structural modifications at positions 13, 16 and 17 of 16β-(m-carbamoylbenzyl)-estradiol on 17β-hydroxysteroid dehydrogenase type 1 inhibition and estrogenic activity
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- 作者：René ; Maltaisa ; b ; Alexandre Trottiera ; b ; Xavier Barbeauc ; d ; Patrick Lagü ; ed ; e ; Martin Perreaulta ; b ; Jean-Franç ; ois Thé ; riaulta ; b ; Sheng-Xiang Lina ; b ; Donald Poiriera ; b ; donald.poirier@crchul.ulaval.ca" class="auth_mail" title="E-mail the corresponding author
- 关键词：Steroid ; Enzyme inhibitor ; Estrogen ; Chemical synthesis ; Estradiol isomer
- 刊名：Journal of Steroid Biochemistry and Molecular Biology
- 出版年：2016
- 出版时间：July 2016
- 年：2016
- 卷：161
- 期：Complete
- 页码：24-35
- 全文大小：2402 K
文摘
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Stereoisomers at positions 13, 16 and 17 of a steroid 17β-HSD1 inhibitor were prepared and characterized.
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Methyl-18 inversion, from β to α face, is harmful to inhibition of 17β-HSD1.
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Methyl-18 inversion, from β to α face, reduces undesirable estrogenic activity.
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Compound 3a provides the best compromise between 17β-HSD1 inhibition and non estrogenicity.
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Two enzyme-compound interactions were observed by molecular modeling.