3β-acetoxy-7β-azido-17,17-ethylenedioxyandrost-5-ene | 936748-34-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-acetoxy-7β-azido-17,17-ethylenedioxyandrost-5-ene
• CAS: 936748-34-4
• 化学式: C₂₃H₃₃N₃O₄
• 分子量: 415.533
• InChiKey: BLPMATMFYYLOQA-GDLCRWSOSA-N

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-7β-azido-17,17-ethylenedioxyandrost-5-ene 在 lithium aluminium tetrahydride 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以70%的产率得到7β-amino-17,17-ethylenedioxyandrost-5-en-3β-ol
  参考文献：
  名称：

  First synthesis of 7α- and 7β-amino-DHEA, dehydroepiandrosterone (DHEA) analogues and preliminary evaluation of their cytotoxicity on Leydig cells and TM4 Sertoli cells

  摘要：

  Efficient syntheses of new DHEA analogues, and their apoptotic and necrotic effects on Leydig cells and TM4 Sertoli cells are described. The key step in the synthetic strategy of 7-amino-DHEA derivatives involves a bromination on C-7 position to give an epimeric mixture of bromides which were substituted by azides and reduced to give 7 alpha- and 7 beta-amino-3 beta-hydroxyandrost-5-en-17-ones. No cytotoxic effect induced by apoptosis mechanism was observed on Leydig and TM4 Sertoli cells by treatment with these amino-DHEA analogues. A necrotic effect was induced only in TM4 Sertoli cells. The best activity was obtained with 70 alpha,beta-aminoandrost-5-en-3 beta-ol and 7 beta-amino-3 beta-hydroxy-androst-5-en-17-one. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.036
• 作为产物：
  描述：

  3β-acetoxy-7ξ-bromo-5-androsten-17-one-17-ethyleneketal 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以29%的产率得到3β-acetoxy-7β-azido-17,17-ethylenedioxyandrost-5-ene
  参考文献：
  名称：

  First synthesis of 7α- and 7β-amino-DHEA, dehydroepiandrosterone (DHEA) analogues and preliminary evaluation of their cytotoxicity on Leydig cells and TM4 Sertoli cells

  摘要：

  Efficient syntheses of new DHEA analogues, and their apoptotic and necrotic effects on Leydig cells and TM4 Sertoli cells are described. The key step in the synthetic strategy of 7-amino-DHEA derivatives involves a bromination on C-7 position to give an epimeric mixture of bromides which were substituted by azides and reduced to give 7 alpha- and 7 beta-amino-3 beta-hydroxyandrost-5-en-17-ones. No cytotoxic effect induced by apoptosis mechanism was observed on Leydig and TM4 Sertoli cells by treatment with these amino-DHEA analogues. A necrotic effect was induced only in TM4 Sertoli cells. The best activity was obtained with 70 alpha,beta-aminoandrost-5-en-3 beta-ol and 7 beta-amino-3 beta-hydroxy-androst-5-en-17-one. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.036