5alpha-雄甾烷-3beta,16beta,17beta-三醇 | 27261-27-4

• 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: 5alpha-雄甾烷-3beta,16beta,17beta-三醇
• 英文名称: 5α-androstane-3β,17β,16β-triol
• 英文别名: 5α-androstane-3β,16β,17β-triol；5α-Androstan-3β,16β,17β-triol；(10S)-3c.16c.17c-Trihydroxy-10r.13c-dimethyl-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3β.16β.17β-Trihydroxy-10.13-dimethyl-5α-gonan；5α-Androstantriol-(3β.16β.17β)；5alpha-Androstane-3beta,16beta,17beta-triol；(3S,5S,8R,9S,10S,13S,14S,16S,17R)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16,17-triol
• CAS: 27261-27-4
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: CXGDRQWRJUSSAR-KMDKCDOHSA-N

物化性质

• 沸点：
  436.1±15.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5alpha-雄甾烷-3beta,16beta,17beta-三醇 、 乙酸酐 在 吡啶 作用下， 生成 5α-androstane-3β,16β,17β-triyl triacetate
  参考文献：
  名称：

  Studies of Steroid Ring D Epoxides of Enol Acetates; A New Synthesis of Estriol and of Androstane-3β,16α,17β-triol¹

  摘要：

  DOI：

  10.1021/ja01640a026
• 作为产物：
  描述：

  (3S,8R,9S,10R,13S,14S,17R)-3,17-二羟基-10,13-二甲基-1,2,3,4,7,8,9,11,12,14,15,17-十二氢环戊烯并[a]菲-16-酮 在 乙醇 、 磷酸 、 乙酸酐 、 镍 、 溶剂黄146 、 铂 作用下， 生成 5alpha-雄甾烷-3beta,16beta,17beta-三醇
  参考文献：
  名称：

  16取代的类固醇；类固醇16,17-酮醇和16,17-乙二醇的空间结构。

  摘要：

  DOI：

  10.1021/ja01170a096

文献信息

• Selective manipulation of steroid hydroxyl groups with boronate esters: efficient access to antigenic C-3 linked steroid–protein conjugates and steroid sulfate standards for drug detection
  作者：Natasha L. Hungerford、Andrew R. McKinney、Allen M. Stenhouse、Malcolm D. McLeod

  DOI：10.1039/b610499a

  日期：——

  The temporary protection of 17alpha-alkyl-5alpha-androstane-3beta,16beta,17beta triols as boronate esters is an efficient method for their regioselective functionalisation. This has been applied to the synthesis of protein-steroid conjugates 7-10 suitable for the development of immunoassays targeting classes of steroids banned from competition in Australian horse racing and other sports. The synthesis

  作为硼酸酯的17alpha-烷基-5alpha-androstane-3beta，16beta，17beta三醇的临时保护是对其区域选择性功能化的有效方法。这已被应用于蛋白质-类固醇结合物7-10的合成，该蛋白-类固醇结合物的开发适用于针对澳大利亚赛马和其他体育比赛中禁止的类固醇的免疫测定。还报道了用作参考标准的类固醇硫酸盐缀合物42和44的合成。
• Microbial hydroxylation of steroids. Part 12. Hydroxylation of testosterone and related steroids by <i>Gnomonia</i><i>fructicola</i> ATCC 11430
  作者：Herbert L. Holland、Frances M. Brown、P. Chinna Chenchaiah、Michael J. Chernishenko、Shaheer H. Khan、J. Appa Rao

  DOI：10.1139/v89-044

  日期：1989.2.1

  The fungus Gnomoniafructicola ATCC 11430 hydroxylates testosterone at C-2β in 40–60% yield. The enzyme involved has been shown to be an inducible CO sensitive, cyanide insensitive oxygenase, with a requirement for theΔ⁴-3-ketosteroid substrate functionality. The use of 2α- and 2β-deuterium labelled substrates has shown that hydrogen loss from C-2 during 2β hydroxylation is isotope dependent and non-stereospecific. This is interpreted in terms of a Δ^2,4-dienolic enzyme-bound intermediate form of the substrate. Keywords: Gnomoniafructicola, hydroxylation, steroids, testosterone.

  真菌Gnomoniafructicola ATCC 11430以40-60%的产率在C-2β处对睾酮进行羟基化。所涉及的酶已被证明是一种可诱导的CO敏感、氰化物不敏感的氧化酶，需要Δ4-3-酮类固醇底物的功能性。使用2α-和2β-氘标记底物表明，在2β羟基化过程中，C-2处的氢损失是同位素依赖的，且不具有立体特异性。这被解释为底物的Δ2,4-二烯醇酶结合中间体形式。关键词：Gnomoniafructicola、羟基化、类固醇、睾酮。
• Pharmaceutical compositions and treatment methods
  申请人：——

  公开号：US20040116359A1

  公开（公告）日：2004-06-17

  The invention provides compositions comprising formula 1 steroids, e.g., 16&agr;-bromo-3&bgr;-hydroxy-5&agr;-androstan-17-one hemihydrate and one or more excipients, typically wherein the composition comprises less than about 3% water. The compositions are useful to make improved pharmaceutical formulations. The invention also provides methods of intermittent dosing of steroid compounds such as analogs of 16&agr;-bromo-3&bgr;-hydroxy-5&agr;-androstan-17-one and compositions useful in such dosing regimens. The invention further provides compositions and methods to inhibit pathogen (viral) replication, ameliorate symptoms associated with immune dysregulation and to modulate immune responses in a subject using certain steroids and steroid analogs. The invention also provides methods to make and use these immunomodulatory compositions and formulations.

  本发明提供了由式 1 类固醇（如 16&agr;-溴-3&bgr;-羟基-5&agr;-雄甾烷-17-酮半水合物）和一种或多种赋形剂组成的组合物，其中组合物通常包含小于约 3% 的水。本发明的组合物可用于制造改进的药物制剂。本发明还提供了类固醇化合物（如 16&agr;-溴-3&bgr;-羟基-5&agr;-雄甾烷-17-酮的类似物）的间歇给药方法以及在这种给药方案中有用的组合物。本发明进一步提供了使用某些类固醇和类固醇类似物抑制病原体（病毒）复制、改善与免疫失调相关的症状和调节受试者免疫反应的组合物和方法。本发明还提供了制造和使用这些免疫调节组合物和制剂的方法。
• Pharmaceutical compositions and treatment methods-6
  申请人：——

  公开号：US20040220161A1

  公开（公告）日：2004-11-04

  The invention provides compositions comprising formula 1 steroids, e.g., 16&agr;-bromo-3&bgr;-hydroxy-5&agr;-androstan-17-one hemihydrate and one or more excipients, typically wherein the composition comprises less than about 3% water. The compositions are useful to make improved pharmaceutical formulations. The invention also provides methods of intermittent dosing of steroid compounds such as analogs of 16&agr;-bromo-3&bgr;-hydroxy-5&agr;-androstan-17-one and compositions useful in such dosing regimens. The invention further provides compositions and methods to inhibit pathogen (viral) replication, ameliorate symptoms associated with immune dysregulation and to modulate immune responses in a subject using certain steroids and steroid analogs. The invention also provides methods to make and use these immunomodulatory compositions and formulations.

  本发明提供了由式 1 类固醇（如 16&agr;-溴-3&bgr;-羟基-5&agr;-雄甾烷-17-酮半水合物）和一种或多种赋形剂组成的组合物，其中组合物通常包含小于约 3% 的水。本发明的组合物可用于制造改进的药物制剂。本发明还提供了类固醇化合物（如 16&agr;-溴-3&bgr;-羟基-5&agr;-雄甾烷-17-酮的类似物）的间歇给药方法以及在这种给药方案中有用的组合物。本发明进一步提供了使用某些类固醇和类固醇类似物抑制病原体（病毒）复制、改善与免疫失调相关的症状和调节受试者免疫反应的组合物和方法。本发明还提供了制造和使用这些免疫调节组合物和制剂的方法。
• Studies of Steroid Ring D Epoxides of Enol Acetates; A New Synthesis of Estriol and of Androstane-3β,16α,17β-triol¹
  作者：Norma S. Leeds、David K. Fukushima、T. F. Gallagher

  DOI：10.1021/ja01640a026

  日期：1954.6