3β-acetoxy-23,24-bisnor-chol-5-en-22-ol | 55509-37-0

• 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-23,24-bisnor-chol-5-en-22-ol
• 英文别名: 3β-acetoxy-23,24-dinorchol-5-en-22-ol；3Beta-Acetoxybisnor-5-cholen-22-ol (>90%)；[(3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-1-hydroxypropan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 55509-37-0
• 化学式: C₂₄H₃₈O₃
• 分子量: 374.564
• InChiKey: FRNBBMYUVKCZCF-BSVQJXIHSA-N

物化性质

• 熔点：
  153-154 °C(Solv: acetone (67-64-1); methanol (67-56-1))
• 沸点：
  470.3±28.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-23,24-bisnor-chol-5-en-22-ol 在 sodium hydroxide 作用下， 生成 (20S)-20-methyl-pregnene-(5)-diol-(3β.21)
  参考文献：
  名称：

  类固醇酸及其转化产物；对3β-羟基-5-胆酸和-bisnor-5-胆酸的硫醇酯进行脱硫。

  摘要：

  DOI：

  10.1021/ja01189a036
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 镍 作用下， 生成 3β-acetoxy-23,24-bisnor-chol-5-en-22-ol
  参考文献：
  名称：

  类固醇酸及其转化产物；对3β-羟基-5-胆酸和-bisnor-5-胆酸的硫醇酯进行脱硫。

  摘要：

  DOI：

  10.1021/ja01189a036

文献信息

• Studies on steroids. LI. Stereoselective introduction of 22- and 24-hydroxyl function in the steroidal side chain.
  作者：MASAJI ISHIGURO、HIROMITSU SAITO、ATSUO SAKAMOTO、NOBUO IKEKAWA

  DOI：10.1248/cpb.26.3715

  日期：——

  Osmium tetroxide oxidation of the 22-olefin (4) and reaction of sodium dimethylsulfonium methylide with the 22-aldehyde (3a) afforded stereoselectively the 22S-and 22R-epoxides (7a and 7b), respectively. Those epoxide can be led to the 22R- and 22S-hydroxy steroides by Grignard reaction. Inversion of the configuration of hydroxyl group on C-22 and C-24 positions was achieved in high yield by means of superoxide displacement reaction.

  四氧化铂对22-烯烃（4）的氧化以及二甲基磺酸钠甲基化合物与22-醛（3a）的反应，分别立体选择性地生成了22S-和22R-环氧化物（7a和7b）。这些环氧化物可以通过格林雅反应转化为22R-和22S-羟基类固醇。在C-22和C-24位羟基构型的反转是通过超氧取代反应实现的，且产率很高。
• Preparation of (25)- and (25)-26-functionalized steroids as tools for biosynthetic studies of cholic acids
  作者：V KHRIPACH、V ZHABINSKII、O KONSTANTINOVA、N KHRIPACH、A ANTONCHICK、A ANTONCHICK、B SCHNEIDER

  DOI：10.1016/j.steroids.2005.02.014

  日期：2005.7

  new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3beta-hydroxy-Delta(5)- or a Delta(4)-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3beta-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides

  从豆甾醇或 (20S) 开始，描述了在环 A 中含有 3β-羟基-Delta(5)-或 Delta(4)-3-酮基官能团的 26-胆甾烷酸和 26-醇的差向异构形式的新合成)-3β-乙酰氧基-pregn-5-en-20-羧酸。所得化合物可用作研究胆酸的标准品。侧链的构建是通过将甾体 23-碘化物连接到由 (2R)- 和 (2S)-3-羟基-2-甲基丙酸酯制备的砜来实现的。使用由 TEMPO 和漂白剂催化的亚氯酸钠，将中间体 26-醇氧化成相应的羧酸，确保保留 C-25 的立体化学和环状部分的官能团。
• Evaluation of Azasterols as Anti-Parasitics
  作者：Ludovic Gros、Silvia Orenes Lorente、Jimenez、Vanessa Yardley、Lauren Rattray、Hayley Wharton、Susan Little、Simon L. Croft、Luis M. Ruiz-Perez、Dolores Gonzalez-Pacanowska、Ian H. Gilbert

  DOI：10.1021/jm060290f

  日期：2006.10.1

  In this article, the design and synthesis of some novel azasterols is described, followed by their evaluation against Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani, and Plasmodium falciparum, the causative agents of human African trypanosomiasis, Chagas disease, leishmaniasis, and malaria, respectively. Some of the compounds showed anti-parasitic activity. In particular, a number of compounds appeared to very potently inhibit the growth of the blood stream form T. b. rhodesiense, with one compound giving an IC50 value of 12 nM. Clear structure activity relationships could be discerned. These compounds represent important leads for further optimization. Azasterols have previously been shown to inhibit sterol biosynthesis in T. cruzi and L. donovani by the inhibition of the enzyme sterol 24-methyltransferase. However, in this case, none of the compounds showed inhibition of the enzyme. Therefore, these compounds have an unknown mode of action.
• Die Synthese von 5α‐Stigmasta‐22,25‐dien‐3β‐ol, 5α‐Stigmast‐22‐en‐3β‐ol und 5α‐Stigmastan‐3β‐ol und ihren 24‐Epimeren
  作者：Wolfgang Sucrow、Marion Slopianka、Penelope Polyzou Caldeira

  DOI：10.1002/cber.19751080415

  日期：1975.4
• SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents
  作者：Federica Gigante、Marcel Kaiser、Reto Brun、Ian H. Gilbert

  DOI：10.1016/j.bmc.2009.06.062

  日期：2009.8

  There is an urgent need for the development of new drugs for the treatment of neglected tropical diseases such as human African trypanosomiasis, Chagas disease and leishmaniasis. Azasterols, have been shown to have activity against the parasites which cause these diseases. In this paper we report synthesis of new azasterols and subsequent analysis of the SAR. The chemistry focused on variations in the ester at the 3 beta-position of the sterol and the position of the nitrogen in the side chain. The data allowed us to derive preliminary pharmacophore models for the activity of the azasterols against the parasites which cause these diseases. (C) 2009 Elsevier Ltd. All rights reserved.