(20α,22β,25R)-3β-Acetoxyfurost-5-ene-26-(p-toluenesulfonate) | 156207-54-4

• 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: (20α,22β,25R)-3β-Acetoxyfurost-5-ene-26-(p-toluenesulfonate)
• 英文别名: (22β,25R)-3β-acetoxyfurost-5-ene-26-(p-toluenesulfonate)
• CAS: 156207-54-4
• 化学式: C₃₆H₅₂O₆S
• 分子量: 612.871
• InChiKey: QYQYSOUDXFKWQW-NVAOWWDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (20α,22β,25R)-3β-Acetoxyfurost-5-ene-26-(p-toluenesulfonate) 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以67%的产率得到(20α,22β,25R)-3β-acetoxy-5-ene-26-azidofurostane
  参考文献：
  名称：

  Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate

  摘要：

  Solasodine acetate, an anticancer steroidal alkaloid, was synthesized from diosgenin in 8 steps with an overall yield of 23%. A key synthetic step involves the formation of 5/6-oxazaspiroketal moiety via hypoiodite-mediated aminyl radical cyclization of a steroidal primary amine. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.002
• 作为产物：
  描述：

  (25R) furost-5-en-3β-acetoxy 26-ol 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以4.62 g的产率得到(20α,22β,25R)-3β-Acetoxyfurost-5-ene-26-(p-toluenesulfonate)
  参考文献：
  名称：

  Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate

  摘要：

  Solasodine acetate, an anticancer steroidal alkaloid, was synthesized from diosgenin in 8 steps with an overall yield of 23%. A key synthetic step involves the formation of 5/6-oxazaspiroketal moiety via hypoiodite-mediated aminyl radical cyclization of a steroidal primary amine. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.002

文献信息

• Synthesis, biological evaluation and molecular docking studies of novel diosgenin derivatives as anti-inflammatory agents
  作者：Sheng-Nan Zhang、Xiao-Dong Mu、Xiao-Fan Zhang、Ming-Zhu Luan、Guang-Qun Ma、Wei Li、Qing-Guo Meng、Xiao-Yun Chai、Gui-Ge Hou

  DOI：10.1016/j.bioorg.2022.105908

  日期：2022.10

  Thirty-two novel DG F-spiroacetal ring-opening derivatives, including 24 acetylated derivatives and 8 nitrogenous derivatives, were designed and synthesized from diosgenin (DG). The cytotoxicity of the novel derivatives was evaluated by MTT assay, except for compounds 4a, 4e, 4i, 4 l, 5a and 5 h, which were potentially cytotoxic to RAW264.7 cells, all the other derivatives had no significant cytotoxicity

  以薯蓣皂苷元（DG）为原料，设计合成了32种新型DG F-螺缩醛开环衍生物，包括24种乙酰化衍生物和8种含氮衍生物。采用MTT法评价了新衍生物的细胞毒性，除化合物4a、4e、4i、4l、5a和5h对RAW264.7细胞具有潜在的细胞毒性外，其余衍生物均无明显细胞毒性。采用Griess方法筛选了新型衍生物的NO释放抑制活性。结果表明，DG乙酰化衍生物的抗炎活性强于含氮衍生物，4a - 4 m在 3 位含有乙酰基的抗炎作用可能比含有游离羟基的5a - 5k更好。在 ELISA 测定中，化合物4 m通过抑制 LPS 激活的 RAW264.7 细胞中 NO 的产生而表现出有效的抗炎活性，IC 50值为 0.449 ± 0.050 μM。对接实验结果表明，4m对p65蛋白具有良好的亲和力。
• A Novel Synthetic Approach from Diosgenin to a 17α‐Hydroxy Orthoester via a Regio‐ and Stereo‐Specific Rearrangement of an Epoxy Ester
  作者：Nisachon Chaosuancharoen、Ngampong Kongkathip、Boonsong Kongkathip

  DOI：10.1081/scc-120028627

  日期：2004.12.31

  A cholesterol model compound, containing 16beta-acetoxy, 17alpha-hydroxy, and (20S, 22R)-epoxy groups was synthesized from diosgenin in 13 steps and was rearranged regio- and stereo-specifically to an orthoester with BF3.Et2O.