甲基7alpha-羟基-3-氧代胆烷酸酯 | 14773-00-3

• 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
• 中文名称: 甲基7alpha-羟基-3-氧代胆烷酸酯
• 中文别名: 7α-羟基-3-酮胆酸甲酯
• 英文名称: methyl 7α-hydroxy-3-oxo-5β-cholan-24-oate
• 英文别名: 5beta-Cholan-24-oic acid, 7alpha-hydroxy-3-oxo-, methyl ester；methyl (4R)-4-[(5R,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 14773-00-3
• 化学式: C₂₅H₄₀O₄
• 分子量: 404.59
• InChiKey: XHRLTYUHWGHDCJ-WZAAVQHPSA-N

物化性质

• 熔点：
  128-129 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  505.7±25.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 保留指数：
  3258

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：

  甲基7alpha-羟基-3-氧代胆烷酸酯 在 吡啶 、 phenyltrimethylammonium tribromide 、 lithium carbonate 、 lithium bromide 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 25,26,27-trisnorcholesta-1,4,6-trien-3-on-24-oic acid methyl ester
  参考文献：
  名称：

  Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis

  摘要：

  We have synthesized a tritiated form of 5beta-cholest-7-ene-3,6-dione (5beta-diketone) of high specific activity (9.2 TBq/mmol) in ten steps from deoxychenocholic acid, which possesses the desired A/B cis ring junction (5beta-H configuration). We have conceived a synthetic pathway which permits labelling by tritiation at the final step and allowing for the introduction of the tritium label into both the side chain and the nucleus. We have examined the ability of insect endocrine glands (prothoracic glands) of Pieris Brassicae to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. No conversion can be detected. In the myriapod Lithobius forficatus only reduction of the 3-ketone can be observed. It seems that the 5beta-diketone is not an intermediate in the ecdysone biosynthetic pathway.

  DOI：

  10.1016/s0040-4020(01)86327-4
• 作为产物：
  描述：

  鹅去氧胆酸 在 盐酸 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 24.84h， 生成 甲基7alpha-羟基-3-氧代胆烷酸酯
  参考文献：
  名称：

  [EN] METHOD AND COMPOSITIONS FOR FORMING A COPPER-CONTAINING COMPLEX AND USES THEREOF
  [FR] PROCÉDÉ ET COMPOSITIONS POUR FORMER UN COMPLEXE CONTENANT DU CUIVRE ET UTILISATIONS CORRESPONDANTES

  摘要：

  提供一种形成含铜络合物的方法，包括将含铜样品与化合物（I）的化合物接触：其中R为-OH或-O-CH3。还提供了一种抑制样品中激酶酶活性的方法，包括将样品与化合物（I）接触。进一步提供了一种给予受试者的药物组合物的方法，其中包括一种化合物（I）的药物组合物，可选择与铜形成络合物。还提供了一种包括与化合物（I）形成络合物的铜的药物组合物。

  公开号：

  WO2019090331A1

文献信息

• A Concise and Stereoselective Synthesis of Squalamine
  作者：Dong-Hui Zhang、Feng Cai、Xiang-Dong Zhou、Wei-Shan Zhou

  DOI：10.1021/ol035062j

  日期：2003.9.1

  [reaction: see text] A short and highly stereoselective synthesis of the novel steroid squalamine (1) was accomplished in nine steps from easily available methyl chenodeoxylcholanate 2. Our synthesis featured improved dehydrogenation of 4 followed by conjugate reduction to construct the trans AB-ring system and efficient asymmetric isopropylation of aldehyde 6 to introduce the C-24R-hydroxyl group

  [反应：参见文本]从易于获得的甲基鹅去氧胆酸甲酯2的九步中完成了新型甾体角鲨胺（1）的短而高度立体选择性的合成。我们的合成具有改善的4脱氢率，然后偶联物还原以构建反式AB环的特点。系统和醛6的有效不对称异丙基化以引入C-24R-羟基。
• Bile acids. LXXIX. synthesis and reduction of 1,4-dien-3-ones of various bile acids
  作者：Mohammed N. Iqbal、William H. Elliott

  DOI：10.1016/0039-128x(89)90022-6

  日期：1989.3

  bile acids (IIa-d), their methyl esters (IIe-h), and their formylated derivatives (IIi-k) were synthesized and their reduction investigated by both catalytic and chemical methods as an alternative route to the synthesis of allo bile acids. Lithium-ammonia reduction proved to be the better method for the reduction of these 1,4-dien-3-ones producing the 3-keto- and 3 beta-hydroxy-allo bile acids (Vb-d)

  合成了各种胆汁酸 (IIa-d) 的 1,4-Dien-3-ones、它们的甲酯 (IIe-h) 和它们的甲酰化衍生物 (IIi-k)，并通过催化和化学方法研究了它们的还原情况，如合成别胆汁酸的另一种途径。锂-氨还原被证明是还原这些 1,4-二烯-3-酮的更好方法，产生 3-酮-和 3-β-羟基-别胆酸 (Vb-d) 和 (VIb-d)产率为 66-72%。
• Emerging Options in the Treatment of Bipolar Disorders
  作者：Michael Berk、Jose Segal、Leigh Janet、Merryll Vorster

  DOI：10.2165/00003495-200161100-00004

  日期：——

  Bipolar disorder is a common and severe condition, and has a clinical outcome that is frequently sub-optimal. Only a small number of therapeutic options are currently available for the disorder. A growing range of novel therapeutic options for the treatment of bipolar disorder are under investigation. These include the anticonvulsants, atypical antipsychotics and options such as the omega-3 fatty acids and transcranial magnetic stimulation. Of the anticonvulsants, lamotrigine is currently the agent for which the greatest amount of controlled clinical data is accumulating, particularly in the depressed and rapid cycling phases of the illness. Olanzapine is currently the atypical antipsychotic with the largest body of evidence in mania, although data is emerging on other atypical antipsychotics including risperidone and ziprasidone. Data regarding the atypical agents in other phases of the illness are awaited. The options available for this difficult to treat condition is increasing with the new range of agents.

  双相情感障碍是一种常见且严重的疾病，其临床结果通常不尽如人意。目前针对该疾病的治疗选择较少。越来越多的新型治疗选项正在研究中，包括抗癫痫药、非典型抗精神病药，以及如omega-3脂肪酸和经颅磁刺激等选项。在抗癫痫药中，拉莫三嗪目前是积累了最多对照临床数据的药物，特别是在抑郁和快速循环发作阶段。奥氮平目前是针对狂躁症有最多证据的非典型抗精神病药物，尽管关于其他非典型抗精神病药物如利培酮和齐拉西酮的数据也在逐渐出现。针对该疾病其他阶段非典型药物的数据尚待发布。随着新药物的出现，治疗这一难治性疾病的选择正在增加。
• Syntheses with stable isotopes: Synthesis of deuterium and¹³C labeled bile acids
  作者：D. L. Hachey、P. A. Szczepanik、O. W. Berngruber、P. D. Klein

  DOI：10.1002/jlcr.2590090412

  日期：1973.10

  A series of 5β-cholanic acids labeled with deuterium in the A ring were prepared by exchange labeling of the corresponding ketone by column chromatography on deuterated alumina. Factors affecting yield and labeling efficiency are discussed. 5β-Cholanic acids labeled with 13C in the carboxyl position were prepared by treatment of the corresponding 23-chloro-24-norcholane with sodium cyanide-13C followed by alkaline hydrolysis of the nitrile. The intermediates in the synthesis were characterized by high resolution NMR spectroscopy. Mass spectra are also reported for the 13C labeled products.

  通过在氚化氧化铝上进行柱层析，对相应的酮进行交换标记，制备了一系列在 A 环中用氘标记的 5β-cholanic 酸。本文讨论了影响产率和标记效率的因素。用氰化钠-13C 处理相应的 23-氯-24-正胆烷，然后碱水解腈，制备了在羧基位置标记 13C 的 5β-Cholanic 酸。合成过程中的中间产物通过高分辨率核磁共振光谱进行了表征。同时还报告了 13C 标记产物的质谱图。
• A Photocleavable Masked Nuclear‐Receptor Ligand Enables Temporal Control of <i>C. elegans</i> Development
  作者：Joshua C. Judkins、Parag Mahanti、Jacob B. Hoffman、Isaiah Yim、Adam Antebi、Frank C. Schroeder

  DOI：10.1002/anie.201307465

  日期：2014.2.17

  The development and lifespan of C. elegans are controlled by the nuclear hormone receptor DAF‐12, an important model for the vertebrate vitamin D and liver X receptors. As with its mammalian homologues, DAF‐12 function is regulated by bile acid‐like steroidal ligands; however, tools for investigating their biosynthesis and function in vivo are lacking. A flexible synthesis for DAF‐12 ligands and masked

  线虫的发育和寿命由核激素受体 DAF-12 控制，DAF-12 是脊椎动物维生素 D 和肝脏 X 受体的重要模型。与其哺乳动物同源物一样，DAF-12 的功能由胆汁酸样甾体配体调节。然而，缺乏研究其生物合成和体内功能的工具。开发了 DAF-12 配体和掩蔽配体衍生物的灵活合成方法，能够精确控制 DAF-12 功能的时间。为了掩蔽配体，引入了 5-甲氧基-N-甲基-2-硝基苯胺 (MMNA) 的光裂解酰胺。 MMNA 掩蔽配体具有生物利用度，在掺入蠕虫体内后，短暂的紫外线照射可用于触发 DAF-12 靶基因的表达，并启动从 DAuer 幼虫到成虫的发育。通过使用可光裂解的 MMNA 掩蔽配体在体内释放 DAF-12 配体和其他小分子信号将使具有精确空间和时间分辨率的功能研究成为可能。