3β-acetoxy-7ξ-bromo-5-androsten-17-one-17-ethyleneketal | 936748-32-2

• 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-7ξ-bromo-5-androsten-17-one-17-ethyleneketal
• 英文别名: 3β-acetoxy-7-bromo-17,17-ethylenedioxyandrost-5-ene
• CAS: 936748-32-2
• 化学式: C₂₃H₃₃BrO₄
• 分子量: 453.417
• InChiKey: USXAVCIIAQWRNO-DVUPJZBUSA-N

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-7ξ-bromo-5-androsten-17-one-17-ethyleneketal 在 吡啶 、 氢氧化钾 、 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 132.33h， 生成 3β-hydroxy-7β-carboxymethyl-5-androsten-17-one
  参考文献：
  名称：

  Preparation of dehydroepiandrosterone, testosterone and progesterone antigens through 7-carboxymethyl derivatives: Characteristics of the antisera to testosterone and progesterone

  摘要：

  Dehydroepiandrosterone, testosterone and progesterone 7-carboxymethyl derivatives were prepared: 7 alpha and 7 beta epimers were separated and coupled to bovine serum albumin. Preliminary studies of the antisera induced by these antigens showed that they have high affinity and good specificity.

  DOI：

  10.1016/0039-128x(80)90037-9

文献信息

• First synthesis of 7α- and 7β-amino-DHEA, dehydroepiandrosterone (DHEA) analogues and preliminary evaluation of their cytotoxicity on Leydig cells and TM4 Sertoli cells
  作者：Marc-Antoine Bazin、Carine Travert、Serge Carreau、Sylvain Rault、Laïla El Kihel

  DOI：10.1016/j.bmc.2007.02.036

  日期：2007.5

  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.