3β-acetoxy-16-benzoyl-17-benzoylhydrazono-5α-androstane | 1263180-95-5

• 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-16-benzoyl-17-benzoylhydrazono-5α-androstane
• CAS: 1263180-95-5
• 化学式: C₃₅H₄₂N₂O₄
• 分子量: 554.729
• InChiKey: QGTHLLOEWUAHQE-VSBGMQNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  41.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  84.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  醋酸去氢表雄酮 在 哌啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3β-acetoxy-16-benzoyl-17-benzoylhydrazono-5α-androstane
  参考文献：
  名称：

  Synthesis and biological evaluation of some nitrogen containing steroidal heterocycles

  摘要：

  epi-Androsterone 1 was converted into its hydrazone derivative through the reaction with hydrazine hydrate 80%. Hydrazonoandrostane derivative 2b reacted with hydrazonoyl halides in the presence of K(2)CO(3) forming the corresponding hydrazopyridazinoandrostane derivatives 6a-d. The 3 beta-acetyl-17-hydrazonoandrostane derivative 2b reacted with a halogen reagent, benzoyl chloride, to form the non-cyclic 16-benzoylated hydrazone 9.On the other hand, compound 2b produced the corresponding pyridazinoandrostane derivatives 11 and 12 via its reaction with phenacyl bromide and chloroacetone respectively. Reaction of the hydrazono derivative 2b with benzaldehyde in the presence of acetic acid drops led to the formation of the benzylidenehydrazonoandrostane derivative 13. The product 14, phosphinom-ethylenehydrazonoandrostane was obtained by the reaction of the derivative 13 with trisdimethylaminophosphine in the presence of dry benzene. The reaction of compound 2b with phenyl isothiocyanate followed by boiling in chloroacetic acid or thioglycolic acid produced the pyrazoloandrostane derivatives 17 and 18 respectively. The biological activity of compounds 6a, 6d, 11, 12, and 15 was evaluated as inhibitor of growth in a human liver carcinoma cell line and doxorubicine was used for comparison. Compounds 15 and 12 showed a higher potency than the other tested compounds. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.09.001