(25R)-5α-cholestane-3β,26-diol | 43204-19-9

• 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: (25R)-5α-cholestane-3β,26-diol
• 英文别名: (25R)-5α-Cholestan-3β,26-diol；(25R)-26-hydroxycholestanol；(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 43204-19-9
• 化学式: C₂₇H₄₈O₂
• 分子量: 404.677
• InChiKey: DKISDYAXCJJSLZ-VCDYLVHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (25R)-5α-cholestane-3β,26-diol 在 硼烷四氢呋喃络合物 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 19.5h， 生成 (25R)-5α-cholestane-3α,15α,26-triol
  参考文献：
  名称：

  Synthesis of the Aglycone of the Shark Repellent Pavoninin-4 Using Remote Functionalization

  摘要：

  The aglycone of shark repellent pavoninin-4, (25R)-5 alpha-cholestan-3 alpha,15 alpha,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3 beta,-26-diol 4(26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy was used as a key step to introduce the C-15 alpha alcohol on a steroid D ring. An efficient synthesis of the 26-hydroxycholesterol from the 16 beta hydroxyl steroid, (25R)cholest-5-ene-3 beta,16 beta,26-triol (3a), is also reported.

  DOI：

  10.1021/ol060079y
• 作为产物：
  描述：

  隐配质 在 盐酸 、 amalgamated zinc 、 溶剂黄146 、 铂 作用下， 生成 (25R)-5α-cholestane-3β,26-diol
  参考文献：
  名称：

  5-Cholestene-3β,26-diol

  摘要：

  DOI：

  10.1021/ja01599a054

文献信息

• Cytochrome P450 27A1 Deficiency and Regional Differences in Brain Sterol Metabolism Cause Preferential Cholestanol Accumulation in the Cerebellum
  作者：Natalia Mast、Kyle W. Anderson、Joseph B. Lin、Yong Li、Illarion V. Turko、Curtis Tatsuoka、Ingemar Bjorkhem、Irina A. Pikuleva

  DOI：10.1074/jbc.m116.774760

  日期：2017.3

  27A1 (CYP27A1 or sterol 27-hydroxylase) is a ubiquitous, multifunctional enzyme catalyzing regio- and stereo-specific hydroxylation of different sterols. In humans, complete CYP27A1 deficiency leads to cerebrotendinous xanthomatosis or nodule formation in tendons and brain (preferentially in the cerebellum) rich in cholesterol and cholestanol, the 5alpha-saturated analog of cholesterol. In Cyp27a1-/-

  细胞色素P450 27A1（CYP27A1或固醇27-羟化酶）是一种普遍存在的多功能酶，可催化不同固醇的区域和立体特异性羟基化。在人类中，完全的CYP27A1缺乏会导致富含胆固醇和胆固醇（5α-饱和的胆固醇类似物）的腱和大脑（最好是在小脑）的腱和大脑中形成脑腱黄瘤病或结节。在Cyp27a1-/-小鼠中，尽管大脑和小脑中的胆固醇含量显着增加，但仍未形成黄瘤。胆固醇生成的机理已经阐明，但其代谢知之甚少，除了CYP27A1可能代谢胆固醇。还不清楚为什么CYP27A1缺乏会导致小脑中胆固醇的优先积累。我们假设胆固醇可能被CYP46A1代谢，脑中主要的胆固醇24-羟化酶。我们在小鼠模型（Cyp27a1-/-，Cyp46a1-/-，Cyp27a1-/-Cyp46a1-/-和两个野生型菌株）和人类脑标本中对固醇以及CYP27A1和CYP46A1进行了定量。还进行了纯化P450的体外实验。我们证明CYP4
• Synthesis of steroidal inhibitors for Mycobacterium tuberculosis
  作者：Luke R. Churchman、James R. Beckett、Lendl Tan、Kyra Woods、Daniel Z. Doherty、Amna Ghith、Paul V. Bernhardt、Stephen G. Bell、Nicholas P. West、James J. De Voss

  DOI：10.1016/j.jsbmb.2024.106479

  日期：2024.5

  Oxidised derivatives of cholesterol have been shown to inhibit the growth of (). The bacteriostatic activity of these compounds has been attributed to their inhibition of CYP125A1 and CYP142A1, two metabolically critical cytochromes P450 that initiate degradation of the sterol side chain. Here, we synthesise and characterise an extensive library of 28 cholesterol derivatives to develop a structure-activity

  胆固醇的氧化衍生物已被证明可以抑制 () 的生长。这些化合物的抑菌活性归因于它们对 CYP125A1 和 CYP142A1 的抑制，这两种代谢关键细胞色素 P450 会引发甾醇侧链的降解。在这里，我们合成并表征了 28 种胆固醇衍生物的广泛库，以开发此类抑制剂的结构-活性关系。评估了候选化合物的 MIC 毒性以及与 CYP125A1 和 CYP142A1 的结合研究
• Synthesis of the Aglycone of the Shark Repellent Pavoninin-4 Using Remote Functionalization
  作者：Hua Gong、John R. Williams

  DOI：10.1021/ol060079y

  日期：2006.5.1

  The aglycone of shark repellent pavoninin-4, (25R)-5 alpha-cholestan-3 alpha,15 alpha,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3 beta,-26-diol 4(26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy was used as a key step to introduce the C-15 alpha alcohol on a steroid D ring. An efficient synthesis of the 26-hydroxycholesterol from the 16 beta hydroxyl steroid, (25R)cholest-5-ene-3 beta,16 beta,26-triol (3a), is also reported.
• 5-Cholestene-3β,26-diol
  作者：Irving Scheer、Malcolm J. Thompson、Erich Mosettig

  DOI：10.1021/ja01599a054

  日期：1956.9