5-Beta-卓兰-24-醇 | 3110-99-4

• 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
• 中文名称: 5-Beta-卓兰-24-醇
• 英文名称: 5β-cholan-24-ol
• 英文别名: 24-hydroxycholane；24-cholanol；cholanol；(10S)-10r.13c-Dimethyl-17c-((R)-4-hydroxy-1-methyl-butyl)-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；10.13-Dimethyl-17β-((R)-4-hydroxy-1-methyl-butyl)-5β-gonan；5β-Cholanol-(24)；5-beta-Cholan-24-OL；(4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentan-1-ol
• CAS: 3110-99-4
• 化学式: C₂₄H₄₂O
• 分子量: 346.597
• InChiKey: ZWJSLCYDYKYAGX-OBUPQJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Beta-卓兰-24-醇 在 五溴化磷 作用下， 生成 24-bromocholane
  参考文献：
  名称：

  Comparative studies of ‘bile salts’. 6. Partial synthesis of coprostanic acid, a ‘stem acid’ of primitive bile salts

  摘要：

  DOI：

  10.1042/bj0520588
• 作为产物：
  描述：

  methyl 5β-cholan-24-oate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以11.1 mg的产率得到5-Beta-卓兰-24-醇
  参考文献：
  名称：

  海七鳃鳗 (Petromyzon marinus) 中非天然硫酸化 5β-胆汁酸衍生物的合成和嗅觉活性。

  摘要：

  合成了多种非天然胆汁酸衍生物 (9a-9f) 并用于检查海七鳃鳗 (Petromyzon marinus) 嗅觉系统检测这些化合物的特异性。这些化合物是硫酸岩藻醇 (PS, 1) 的类似物，是海七鳃鳗迁移信息素的一种成分。C5 的立体化学构型（即 5alpha 与 5beta）以及胆汁酸衍生的类固醇骨架的氧化程度和位点（羟基化或酮化）通过使用嗅觉图记录筛选嗅觉活性的化合物来评估。5beta-Petromyzonol 硫酸盐 (9a) 在亚纳摩尔浓度下引起相当大的嗅觉反应。此外，含氧量较低的系统（即 9b-9e）会引起嗅觉反应，尽管效力较低。还检查了海七鳃鳗性信息素模拟物 9f（5beta-3-ketopetromyzonol 硫酸盐），发现其产生的嗅觉反应要低得多。用 9a 和 PS (1) 进行的混合研究表明刺激是通过类似的激活模式发生的，这表明在海七鳃鳗嗅觉中识别同种异体构型（即 5a

  DOI：

  10.1016/j.steroids.2010.11.010

文献信息

• STEROIDS AND RELATED NATURAL PRODUCTS: XXXI. SELECTIVE REDUCTION OF ESTERS. PART B. CARBONATES
  作者：George R. Pettit、William J. Evers

  DOI：10.1139/v66-192

  日期：1966.6.1

  trifluoride, of 3-oxo-17β-benzoyloxy-5α-androstane (III) into 3β-hydroxy-17β-benzoyloxy-5α-androstane (IV) and of reserpine (V) into alcohol VI. With aryl–carbon–oxygen bonds of the ketone VII or alcohol IXa type, reaction with sodium borohydride– boron trifluoride was shown, in general, to cause reductive fission of the benzyl–oxygen linkage (e.g. X → XI). An exception was noted in the case of tertiary

  以前，硼氢化钠 - 三氟化硼等试剂已被证明能够将典型的脂肪族酯和内酯还原为相应的醚衍生物。在相同的反应条件下，多种苯甲酸酯（Ib、IIb、III 和 V）基本不受影响。通过硼氢化钠 - 三氟化硼将 3-oxo-17β-benzoyloxy-5α-androstane (III) 转化为 3β-hydroxy-17β-benzoyloxy-5α-androstane (IV) 和利血平 (V ) 变成酒精 VI。对于酮 VII 或醇 IXa 型的芳基-碳-氧键，与硼氢化钠-三氟化硼的反应通常会导致苄基-氧键（例如 X → XI）的还原裂变。在含有可用β-氢（例如IXc）的叔苄醇的情况下注意到了一个例外。这里，例如，脱水产生烯烃 XIIb 似乎是更有利的反应过程。硼氢化钠反应性的显着差异 - ...
• Genetic and management factors that influence the susceptibility of cattle to<i>Mycobacterium bovis</i>infection
  作者：Clive J. C. Phillips、Charles R. W. Foster、Pat A. Morris、Rachel Teverson

  DOI：10.1079/ahrr200236

  日期：2002.6

  Genetic variation in the susceptibility of cattle toMycobacterium bovisinfection exists in differences between families and species, but not breeds. Susceptibility toM. bovisinfection increases with age of cattle. Natural exposure toM. bovisor environmental mycobacteria may assist in the development of specific immunity, but there is no direct evidence for such immunological priming of tuberculosis resistance in cattle. This has, however, been demonstrated in humans and other animals. Since non-specific mechanisms have a role in protective immunity, developing an effective vaccine will be difficult, even though some protection of other species has been achieved. Immunological suppression in the periparturient period can produce anergic reactors, which may act as a constant source of infection for cattle-to-cattle transmission. Circumstantial evidence suggests that an adequate intake of mineral, vitamin and protein reduces the susceptibility of cattle. Although weather patterns have been implicated in the susceptibility of herds toM. bovisinfection, there is insufficient information to determine the risk factors precisely. It is concluded that some reduction in the susceptibility of cattle toM. bovisinfection can be achieved by modifications to the management system to minimize risk factors, but that a considerable amount of further research is required.

  摘要 牛对牛分枝杆菌感染敏感性的遗传变异存在家系和物种之间的差异，但不存在品种之间的差异。对牛分枝杆菌感染的易感性随牛的年龄而增加。牛分枝杆菌环境分枝杆菌的自然暴露可能有助于特异性免疫力的发展，但目前还没有直接证据表明牛对结核病的抵抗力是由这种免疫启动的。不过，这在人类和其他动物身上得到了证实。由于非特异性机制在保护性免疫中发挥作用，因此，尽管其他物种已经获得了一定程度的保护，但开发有效疫苗仍将十分困难。围产期的免疫抑制会产生过敏反应者，这可能成为牛与牛之间传播的持续感染源。间接证据表明，摄入充足的矿物质、维生素和蛋白质可降低牛的易感性。虽然天气模式与牛群对牛海绵状瘤病毒感染的易感性有关，但没有足够的信息来准确确定风险因素。结论是，通过调整管理系统以尽量减少风险因素，可在一定程度上降低牛群对牛海绵状瘤病毒感染的易感性，但仍需开展大量的进一步研究。
• Methanesulfonate Esters of Cholane1 Alcohols1All cholane derivatives mentioned in this paper ere 5β-cholanca.
  作者：Frederic C. Chang

  DOI：10.1002/jps.2600530904

  日期：1964.9

  Some methanesulfonate esters of cholane alcohols derived from desoxycholic acid have been prepared and submitted for screening as antitumor agents. Infrared spectra of the dimesylates have distinctive patterns in the 870 to 1000 cm. −1 region, each of which is shown to be virtually superimposable on a composite spectrum of a pair of corresponding mono-mesylates. Antitumor screening test results indicate

  已经制备了一些由脱氧胆酸衍生的胆甾醇的甲磺酸酯，并将其作为抗肿瘤剂进行筛选。二甲基化产物的红外光谱在870至1000厘米范围内具有独特的图案。-1区，每个区显示为实际上可重叠在一对相应的单甲磺酸酯的复合光谱上。抗肿瘤筛选测试结果表明3α，12α-和12α，24化合物对测试动物无活性且无害，但3α，24-异构体的毒性却很大。
• Preparation of alkyl chlorides, acid chlorides, and amides using polymer-supported phosphines and carbon tetrachloride: mechanism of these reactions
  作者：Charles R. Harrison、Philip Hodge、Barry J. Hunt、Ezzatollah Khoshdel、Graham Richardson

  DOI：10.1021/jo00169a022

  日期：1983.10
• Cosalane Analogs with Enhanced Potencies as Inhibitors of HIV-1 Protease and Integrase
  作者：Mark Cushman、W. Marek Golebiewski、Yves Pommier、Abhijit Mazunder、Diane Reymen、Erik De Clercq、Lisa Grahm、William G. Rice

  DOI：10.1021/jm00003a007

  日期：1995.2

  Several new analogues of the novel anti-HIV agent cosalane have been synthesized and evaluated as inhibitors of HIV-1 integrase and protease, HIV-1 replication, HIV-1 and HIV-2 cytopathicity, HIV-1- and HIV-2-mediated syncytium formation, and cytopathicity of a variety of human pathogenic viruses. The congeners displayed enhanced potencies relative to cosalane itself as inhibitors of HIV-1 integrase and protease. The two most potent analogues against HIV-1 integrase displayed IC50 values of 2.2 mu M, while the three most potent compounds against HIV-1 protease had IC50 values in the 0.35-0.39 mu M range. In addition to its activity against HIV-1 and HIV-2 cytopathicity, cosalane inhibited the cytopathic effects of herpes simplex virus-1, herpes simplex virus-2, and human cytomegalovirus at concentrations that were well below the cytotoxic concentrations. Potentially useful antiviral activities were also revealed for some of the new cosalane congeners against influenza virus, Junin virus, and Tacaribe virus.