(24R)-27-nor-5β-cholestane-3α,7α,12α,24,26-pentol | 67392-10-3

• 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
• 英文名称: (24R)-27-nor-5β-cholestane-3α,7α,12α,24,26-pentol
• 英文别名: (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R,5R)-5,7-dihydroxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
• CAS: 67392-10-3
• 化学式: C₂₆H₄₆O₅
• 分子量: 438.648
• InChiKey: PBXYLMVLLSYZLN-ILLINABOSA-N

物化性质

• 沸点：
  617.1±55.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 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：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3α,7α,12α-trihydroxy-5β-cholan-24-al 在 3,4-二氢-2H-吡喃 、 盐酸 、 lithium aluminium tetrahydride 、 碘 、 铜 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 11.0h， 生成 (24R)-27-nor-5β-cholestane-3α,7α,12α,24,26-pentol
  参考文献：
  名称：

  Kuramoto, Taiju; Noma, Yukio; Hoshita, Takahiko, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 4, p. 1330 - 1334

  摘要：

  DOI：

文献信息

• A new chiral synthesis of bullfrog bile sterol 5β-ranol
  作者：Don W. Harney、Theodore A. Macrides

  DOI：10.1039/a607850h

  日期：——

  (24R)-27-Nor-5β-cholestane-3α,7α ,12α,24,26-pentol (5β-ranol) has been synthesised by the Wittig olefinic coupling of a steroidal module and a side-chain module followed by reduction and deprotection. The steroidal module is derived from cholic acid by a one-carbon degradation of the side chain to produce norcholic acid followed by the loss of a second carbon in an iododecarboxylation and then synthesis of the triphenylphosphonium iodide. The side-chain module is derived from (S)-(-)-butane-1,2,4-triol by benzylidene protection of the 2,4-diol followed by Swern oxidation to the aldehyde. This general synthetic scheme could be used to produce a range of bile sterols with the (24R)-hydroxy moiety which may have significant hepatoprotective activity against liver damage induced by free radicals or reactive metabolites.

  (24R)-27-去甲-5δ-胆甾烷-3δ±,7δ±,12δ±,24,26-戊醇（5δ²-ranol）是通过一个甾体模块和一个侧链模块的维蒂希烯烃偶联，然后进行还原和脱保护而合成的。甾体模块来自胆酸，通过侧链的一碳降解生成去甲胆酸，然后在碘羧化过程中失去第二个碳，最后合成碘化三苯基膦。侧链模块来自(S)-(-)-丁烷-1,2,4-三醇，通过对 2,4-二醇进行亚苄基保护，然后通过斯韦尔恩氧化反应生成醛。 这种通用合成方案可用于生产一系列具有 (24R)- 羟基分子的胆固醇，这些胆固醇可能对自由基或活性代谢物引起的肝损伤具有显著的保肝活性。
• BILE ALCOHOL AND DRUG CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：TSUMURA CO., LTD.

  公开号：EP0489933A1

  公开（公告）日：1992-06-17

  A novel bile alcohol of general formula (I), having an efficacious physiological activity and being specified in the configurations of particularly the 20-, 24- and 25-positions; formula (I) wherein one of the groups R₁ and R₂ represents a group of formula (A) or (B) while the other represents -OH or -H; R₃ and R₄ represent each -CH₂OH, -CH₃ or -CH₂OSO₃Na; or alternatively R₂ and R₃ are combined together to represent -OCH₂-, R₂ and R₄ are combined together to represent -OCH₂-, or R₃ and R₄ are combined together to represent -CH₂OCH₂-; provided that R₃ and R₄ do not represent -CH₃ at the same time and that R₁ represents -OH or -H and R₂ represents the group of formula (A) or (B) when R₃ and R₄ represent -CH₂OH at the same time. A drug containing the bile alcohol, including those wherein R₃ and R₄ in the above formula (I) represent each -H, -CH₂OH, -CH₃ or -CH₂OSO₃Na (except for the case where both R₃ and R₄ represent -H at the same time), and 3α 7α, 12α, 24-tetrahydroxy-5α- or -5β-cholane is efficacious as a cerebral function protective agent, cholagogue, cell activator, microcirculation improver, antiarteriosclerotic agent, antihyperlipemia drug, hepatic function improver, anti-inflammatory drug, antithrombotic drug and hypertensive.

  通式（I）的新胆醇具有有效的生理活性，特别是在20、24和25位的构型中进行了指定。其中，R₁和R₂中的一个代表公式（A）或（B）的基团，而另一个代表-OH或-H；R₃和R₄分别代表-CH₂OH、-CH₃或-CH₂OSO₃Na；或者R₂和R₃结合在一起代表-OCH₂-，R₂和R₄结合在一起代表-OCH₂-，或者R₃和R₄结合在一起代表-CH₂OCH₂-；前提是R₃和R₄不能同时表示-CH₃，而且当R₃和R₄同时表示-CH₂OH时，R₁表示-OH或-H，R₂表示公式（A）或（B）的基团。含有胆醇的药物，包括上述公式（I）中R₃和R₄分别表示-H、-CH₂OH、-CH₃或-CH₂OSO₃Na的药物（除了R₃和R₄同时表示-H的情况），以及3α 7α，12α，24-四羟基-5α-或-5β-胆烷作为脑功能保护剂、胆汁促进剂、细胞活化剂、微循环改善剂、抗动脉硬化药、降脂药、肝功能改善剂、抗炎药、抗血栓药和降压药具有有效性。
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.