3α,22(S),23-trihydroxy-24-nor-5α-cholan-6-one | 1461716-34-6

• 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: 3α,22(S),23-trihydroxy-24-nor-5α-cholan-6-one
• 英文别名: (22S)-3α,22,23-trihydroxy-24-nor-5α-cholan-6-one；(3R,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3S)-3,4-dihydroxybutan-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 1461716-34-6
• 化学式: C₂₃H₃₈O₄
• 分子量: 378.552
• InChiKey: YCHJEDKUCKXGGR-GHBMPZNLSA-N

物化性质

• 沸点：
  543.1±30.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  猪去氧胆酸 在 吡啶 、 盐酸 、 sodium periodate 、 重铬酸吡啶 、 碘苯二乙酸 、 ruthenium(III) chloride trihydrate 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 3α,22(S),23-trihydroxy-24-nor-5α-cholan-6-one
  参考文献：
  名称：

  Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor

  摘要：

  Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5 alpha-cholestan-6-one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-alpha, interleukin (IL)-1 beta, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.055

文献信息

• Synthesis and Structural Determination of New Brassinosteroid 24-Nor-5α-Cholane Type Analogs
  作者：Jocelyn Oyarce、Vanessa Aitken、César González、Karoll Ferrer、Andrés F. Olea、Teodor Parella、Luis Espinoza Catalán

  DOI：10.3390/molecules24244612

  日期：——

  following a previous reported method, benzoylated derivatives and both S and R brassinosteroids analogs were synthesized. All synthesized compounds were completely characterized by NMR spectroscopy, and HRMS of new compounds are also given. In conclusion, a synthetic route for preparation of new analogs of brassinosteroids of 24-norcholane type and R configuration at C22 were described. It is expected

  天然油菜素类固醇具有 22R、23R 构型，这对生物活性来说是必不可少的。因此，有趣的是阐明具有短侧链的油菜素类固醇的活性是否取决于 C22 构型。在此，我们描述了在 C22 处具有 24-降胆烷型侧链和 R 构型的新油菜素类固醇类似物的合成。初始反应是末端烯烃的二羟基化，产生 S/R 差向异构体。测试了三种不同的方法以评估获得的 S/R 比和反应产率。结果表明，Upjohn 二羟基化反应是最具选择性的反应，S/R 比为 1.0:0.24，而 Sharpless 反应导致 S/R 为 1.0:0.90 的混合物，产率为 95%。使用后一种混合物并遵循先前报道的方法，合成了苯甲酰化衍生物和 S 和 R 油菜素类固醇类似物。所有合成的化合物均通过核磁共振光谱进行了完全表征，并给出了新化合物的 HRMS。总之，描述了用于制备 24-降胆烷类型和 C22 上的 R 构型的油菜素类固醇的新类似物的合成路线。预计这将有助于阐明
• Synthesis of 2-Deoxybrassinosteroids Analogs with 24-nor, 22(S)-23-Dihydroxy-Type Side Chains from Hyodeoxycholic Acid
  作者：Rodrigo Carvajal、Cesar González、Andrés Olea、Mauricio Fuentealba、Luis Espinoza

  DOI：10.3390/molecules23061306

  日期：——

  separated and the absolute configuration at the C22 carbon for the main product 21a was elucidated by single crystal X-ray diffraction analysis of the benzoylated derivative 22. Finally, lactonization of 21a through a Baeyer-Villiger oxidation of triacetylated derivative 23, using CF₃CO₃H/CHCl₃ as oxidant system, leads to lactones 24 and 25 in 35% and 14% yields, respectively. Deacetylation of these

  天然油菜素类固醇广泛存在于植物界，众所周知它们在调节植物生长中起着重要作用。在这项研究中，合成了两个具有较短侧链但保持二醇功能的新型油菜素类固醇类似物。因此，描述了3α-羟基-24-nor，22，23-二羟基-5α-胆甾烷侧链类型的2-脱氧油菜甾醇类似物的合成。起始原料是来自猪去氧胆酸（4）的衍生物，按照先前报道的五步路线获得的总产率为59％。该中间体的侧链通过氧化脱羧改性，得到C22-C23位的末端烯烃（化合物20），随后使烯烃二羟基化。所得的21a的差向异构混合物 分离21b，并通过苯甲酰化衍生物22的单晶X射线衍射分析阐明主要产物21a的C 22碳的绝对构型。最后，使用CF 3 CO 3 H通过三乙酰化衍生物23的Bae​​yer-Villiger氧化将21a内酯化。用/ CHCl 3作氧化剂体系，分别得到内酯24和25，产率分别为35％和14％。这些化合物的脱乙酰基导致2-脱氧油菜
• Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor
  作者：Ya-Xi Yang、Long-Tai Zheng、Jing-Jing Shi、Bo Gao、Yan-Ke Chen、Hui-Chi Yang、Hong-Li Chen、Yuan-Chao Li、Xue-Chu Zhen

  DOI：10.1016/j.bmcl.2013.12.055

  日期：2014.2

  Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5 alpha-cholestan-6-one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-alpha, interleukin (IL)-1 beta, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model. (C) 2013 Elsevier Ltd. All rights reserved.