4-([(3α,5β,7α,12α)-7,12-bis(formyloxy)-24-oxo-24-[(3β,22E)-stigmasta-5,22-dien-3-yloxy]cholan-3-yl]oxy)-4-oxobutanoic acid | 1261131-71-8

• 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: 4-([(3α,5β,7α,12α)-7,12-bis(formyloxy)-24-oxo-24-[(3β,22E)-stigmasta-5,22-dien-3-yloxy]cholan-3-yl]oxy)-4-oxobutanoic acid
• CAS: 1261131-71-8
• 化学式: C₅₉H₉₀O₁₀
• 分子量: 959.358
• InChiKey: NVLVPZNMRQFMIT-CHIANSNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.51
• 重原子数：
  69.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  142.5
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-([(3α,5β,7α,12α)-7,12-bis(formyloxy)-24-oxo-24-[(3β,22E)-stigmasta-5,22-dien-3-yloxy]cholan-3-yl]oxy)-4-oxobutanoic acid 、 C₁₈H₂₇NO₄ 在 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以86%的产率得到(trans)-(3α,5β,7α,12α)-7,12-bis(formyloxy)-24-oxo-24-[(3β,22E)-stigmasta-5,22-dien-3-yloxy]cholan-3-yl 2-(4-(2-[(ethoxycarbonyl)amino]ethoxy)benzyl)cyclohexyl butanedioate
  参考文献：
  名称：

  Steroid conjugates: Synthesis and preliminary biological testing of pro-juvenoids

  摘要：

  A series of 10 new pro-juvenoids (juvenogens, insect hormonogenic compounds, pro-drug-like agents) was synthesized using isomeric synthetic juvenoids (insect juvenile hormone analogs) and steroid molecules as patterns modifying parts of the complex hormonogenic molecules. In addition, several new synthons were prepared, which were required by the designed synthetic protocol to achieve the target molecules. These pro-juvenoids were subjected to the topical screening tests and to the drinking assays on the red firebug (Pyrrhocoris apterus), a convenient model laboratory phytophagous insect. Simple and efficient synthetic procedures for the preparation of the target pro-juvenoids and their synthons are presented. Furthermore, the biological activity of the pro-juvenoids in comparison with the activity of their parent juvenoids and that of several commercially available agents is demonstrated. Juvenoids and pro-juvenoids may replace toxic insecticides persistent in the insect pest control because they have no adverse effects on non-target organisms and/or human. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.013
• 作为产物：
  描述：

  丁二酸酐 、 (3β,22E)-stigmasta-5,22-dien-3-yl (3α,5β,7α,12α)-7,12-bis(formyloxy)-2-hydroxycholan-24-oate 在 吡啶 、 4-二甲氨基吡啶 、 盐酸 作用下， 以 吡啶 、 水 为溶剂， 反应 96.0h， 以72%的产率得到4-([(3α,5β,7α,12α)-7,12-bis(formyloxy)-24-oxo-24-[(3β,22E)-stigmasta-5,22-dien-3-yloxy]cholan-3-yl]oxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Steroid conjugates: Synthesis and preliminary biological testing of pro-juvenoids

  摘要：

  A series of 10 new pro-juvenoids (juvenogens, insect hormonogenic compounds, pro-drug-like agents) was synthesized using isomeric synthetic juvenoids (insect juvenile hormone analogs) and steroid molecules as patterns modifying parts of the complex hormonogenic molecules. In addition, several new synthons were prepared, which were required by the designed synthetic protocol to achieve the target molecules. These pro-juvenoids were subjected to the topical screening tests and to the drinking assays on the red firebug (Pyrrhocoris apterus), a convenient model laboratory phytophagous insect. Simple and efficient synthetic procedures for the preparation of the target pro-juvenoids and their synthons are presented. Furthermore, the biological activity of the pro-juvenoids in comparison with the activity of their parent juvenoids and that of several commercially available agents is demonstrated. Juvenoids and pro-juvenoids may replace toxic insecticides persistent in the insect pest control because they have no adverse effects on non-target organisms and/or human. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.013