methyl 3α-hydroxy-6-oxo-5α-cholan-24-oate | 34186-19-1

• 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: methyl 3α-hydroxy-6-oxo-5α-cholan-24-oate
• 英文别名: 3α-hydroxy-6-oxo-5α-cholanoic acid-(24)-methyl ester；3α-Hydroxy-6-oxo-5α-cholansaeure-(24)-methylester；Methyl 3alpha-hydroxy-6-oxo-5alpha-cholanoate；methyl (4R)-4-[(3R,5S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 34186-19-1
• 化学式: C₂₅H₄₀O₄
• 分子量: 404.59
• InChiKey: PDEKSQPGUZKWQD-FEWOOJTKSA-N

物化性质

• 沸点：
  505.7±25.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3α-hydroxy-6-oxo-5α-cholan-24-oate 在 吡啶 、 sodium periodate 、 碘苯二乙酸 、 ruthenium(III) chloride trihydrate 、 silica gel 、 copper(II) sulfate 作用下， 以 四氯乙烯 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 2a,3a-dihydroxy-24-nor-5a-chol-22-en-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
• 作为产物：
  描述：

  猪去氧胆酸 在 盐酸 、 sodium tetrahydroborate 、 硫酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 75.0h， 生成 methyl 3α-hydroxy-6-oxo-5α-cholan-24-oate
  参考文献：
  名称：

  获得三个已知的油菜素类固醇类似物和全NMR光谱表征的脱氧胆酸的结构修饰。

  摘要：

  一种获得已知油菜素类固醇类似物的改进的合成路线，即2α，3α-二羟基-6-氧代-5α-cholan-24-oate（11）甲基，3α-羟基-6-氧代-7-oxa-5α-cholan的甲基描述了来自猪脱氧胆酸（4）的-24-油酸酯（15）和3α-羟基-6-氧杂-7-氧代-5α-胆烷-24-甲基甲酯（16），其保持天然侧链。在另一种方法中，通过用NaBH 3进行立体选择性还原，将在氧化去氧胆酸甲酯5中获得的二氧化产物6几乎定量地转化为目标单酮7，使该合成路线的总产率提高到96.8％。通过1D和2D异核相关gs-HSQC和gs-HMBC技术，完成了这项工作中合成的所有化合物的完整1 H-和（13）C-NMR分配。从而，

  DOI：

  10.3390/molecules21091139

文献信息

• Studies on steroidal plant-growth regulators. A new route for the efficient synthesis of the 2α,3α-dihydroxy-7-oxa-6-oxo-<scp>B</scp>-homo structural unit of brassinolide
  作者：Wei-Shan Zhou、Biao Jiang、Xin-Fu Pan

  DOI：10.1039/c39880000791

  日期：——

  A highly regioselective formation of steroidal 7-oxa lactone rings via ozone oxidation of enol silyl ethers is described.

  甾-7-氧杂内酯环的甲高度选择性形成经由烯醇甲硅烷基醚的臭氧氧化进行说明。
• [EN] NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF<br/>[FR] STÉROÏDES NEUROACTIFS, COMPOSITIONS ET LEURS UTILISATIONS
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2013036835A1

  公开（公告）日：2013-03-14

  Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, wherein Z is a group of the formula (i), (ii), (iii), (iv), or (v), and wherein L1, L2, L3, X1, X2, Y, Rz4, Rz5, Rz6, n, R1, R2, R3a, R3b, R4a, R4b, R6a, R6b, R7a, R7b, R11a, R11b, R14, R17, R19, R20, R23a, R23b, and R24 are as defined herein, and pharmaceutical compositions thereof. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of CNS-related conditions in mammals.

  根据公式（I）提供化合物及其药学上可接受的盐，其中Z是公式（i）、（ii）、（iii）、（iv）或（v）的基团，L1、L2、L3、X1、X2、Y、Rz4、Rz5、Rz6、n、R1、R2、R3a、R3b、R4a、R4b、R6a、R6b、R7a、R7b、R11a、R11b、R14、R17、R19、R20、R23a、R23b和R24如本文所定义，并且其药物组合物。本发明的化合物被认为对哺乳动物的多种与中枢神经系统相关的疾病的预防和治疗有用。
• NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
  申请人：SAGE THERAPEUTICS, INC.

  公开号：US20160022701A1

  公开（公告）日：2016-01-28

  Provided are methods of evaluating or treating a patient, e.g., a patient having a disorder described herein, comprising: a) optionally, acquiring a patient sample; b) acquiring an evaluation of and/or evaluating the sample for an alteration in the level S24(S)-hydroxycholesterol compared to a reference standard.

  提供了评估或治疗患者的方法，例如，患有本文所述疾病的患者，包括：a) 可选地，获取患者样本；b) 获取对样本的评估和/或评估其S24(S)-羟基胆固醇水平与参考标准相比是否发生改变。
• Synthesis of Five Known Brassinosteroid Analogs from Hyodeoxycholic Acid and Their Activities as Plant-Growth Regulators
  作者：María Duran、Cesar González、Alison Acosta、Andrés Olea、Katy Díaz、Luis Espinoza

  DOI：10.3390/ijms18030516

  日期：——

  that these compounds should possess to exhibit this biological activity have been studied. In this work, a series of known BR analogs 5-15, were synthesized starting from hyodeoxycholic acid 4, and maintaining the alkyl side chain as cholic acid or its methyl ester. The growth-promoting effects of brassinolide (1) and synthesized analogs were evaluated by using the rice lamina inclination assay at concentrations

  油菜素类固醇（BRs）是促进不同植物器官和组织生长的植物激素。研究了这些化合物应具有的具有这种生物活性的结构要求。在这项工作中，从猪去氧胆酸4开始合成了一系列已知的BR类似物5-15，并保持烷基侧链为胆酸或其甲基酯。在1×10-8-1×10-6 M的浓度范围内，通过水稻叶片倾斜试验评估了油菜素内酯（1）和合成的类似物的促生长作用。我们的结果表明，在此浓度范围内，诱导的弯曲水稻幼苗的角度随BRs浓度的增加而增加。对活性进行的分析（在最低测试浓度下测定）的BR结构表明，2α，这些化合物的植物生长活性需要油菜素内酯中存在的3α-二羟基-7-氧杂-6-酮部分，这是通过一些结构-活性关系研究提出的。通过显微镜分析评价化合物8对细胞伸长的作用，结果表明类似物8的生长促进作用主要是由于近侧的细胞伸长，而不是细胞数目的增加。
• Potential bile acid metabolites. 20. A new synthetic route to stereoisomeric 3,6,-dihydroxy- and 6-hydroxy-5α-cholanoic acids
  作者：Takashi Iida、Tamaaki Tamaru、Frederic C. Chang、Toshifumi Niwa、Junichi Goto、Toshio Nambara

  DOI：10.1016/0039-128x(93)90039-p

  日期：1993.8

  An improved procedure for the syntheses of stereoisomeric 3,6-dihydroxy- and 6-hydroxy-5 alpha-cholanoic acids (and their methyl esters) is described. The principal reactions employed are those reported in the preceding paper of this series, with the commercially available hyodeoxycholic acid as starting material. The final step in the procedure is the reduction of the key 5 alpha C-6 ketones with

  描述了一种合成立体异构体3,6-二羟基-和6-羟基-5α-胆酸（及其甲酯）的改进方法。所采用的主要反应是该系列先前论文中报道的反应，以市售的猪去氧胆酸为起始原料。该方法的最后一步是用立体选择性赤道试剂Li / NH3 / MeOH或轴向试剂Zn（BH4）2还原关键的5个αC-6酮。通过薄层色谱，高效液相色谱和气-液色谱迁移率，1H和13C核磁共振谱对制备的6-单羟基化和3,6-二羟基化立体异构体的分析结果进行讨论。 5 beta系列的相应化合物。