23,24-dinorursodeoxycholic acid | 254096-14-5

• 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: 23,24-dinorursodeoxycholic acid
• 英文别名: Dinorursodeoxycholic acid；(2S)-2-[(3R,5S,7S,8R,9S,10S,13S,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid
• CAS: 254096-14-5
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: WQUYUZJNAIWNRJ-ONVGLGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  23,24-dinorursodeoxycholic acid 在 吡啶 、 盐酸 、 三甲基氯硅烷 作用下， 反应 0.33h， 生成
  参考文献：
  名称：

  方便的二壬酸的合成：壬酸腈的氧化水解。

  摘要：

  我们报告了一种简便的方法，可通过氧化水解与一步法从nor酸腈中以合理至良好的产率合成双壬酸（23,24-dinor-5beta-cholan-22-oic酸，pregnane-20-羧酸）叔丁醇钾存在下的氧气。该方法分两步逐步除去胆汁酸侧链中的两个碳原子。已经制备了对应于几种常见胆汁酸的双丁诺酸，并通过光谱法确认了它们的结构。这种简单的合成双降nor酸的方法可能有助于其代谢研究。

  DOI：

  10.1016/s0039-128x(99)00064-1
• 作为产物：
  描述：

  (3alpha,5beta,7beta)-3,7-二羟基-24-去甲胆烷-23-腈 在 potassium tert-butylate 、 18-冠醚-6 、 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 以1.36 g的产率得到23,24-dinorursodeoxycholic acid
  参考文献：
  名称：

  方便的二壬酸的合成：壬酸腈的氧化水解。

  摘要：

  我们报告了一种简便的方法，可通过氧化水解与一步法从nor酸腈中以合理至良好的产率合成双壬酸（23,24-dinor-5beta-cholan-22-oic酸，pregnane-20-羧酸）叔丁醇钾存在下的氧气。该方法分两步逐步除去胆汁酸侧链中的两个碳原子。已经制备了对应于几种常见胆汁酸的双丁诺酸，并通过光谱法确认了它们的结构。这种简单的合成双降nor酸的方法可能有助于其代谢研究。

  DOI：

  10.1016/s0039-128x(99)00064-1

文献信息

• Bile acid toxicity structure–activity relationships: Correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A)
  作者：Ruchika Sharma、Ferenc Majer、Vijaya Kumar Peta、Jun Wang、Ray Keaveney、Dermot Kelleher、Aideen Long、John F. Gilmer

  DOI：10.1016/j.bmc.2010.07.030

  日期：2010.9

  The molecular mechanisms and interactions underlying bile acid cytotoxicity are important to understand for intestinal and hepatic disease treatment and prevention and the design of bile acid-based therapeutics.Bile acid lipophilicity is believed to be an important cytotoxicity determinant but the relationship is not well characterized. In this study we prepared new azido and other lipophilic BAs and altogether assembled a panel of 37 BAs with good dispersion in lipophilicity as reflected in RPTLC R-Mw. The MTT cell viability assay was used to assess cytotoxicity over 24 h in the HET-1A cell line (oesophageal). RMw values inversely correlated with cell viability for the whole set (r(2) = 0.6) but this became more significant when non-acid compounds were excluded (r(2) = 0.82, n = 29). The association in more homologous subgroups was stronger still (r(2) > 0.96). None of the polar compounds were cytotoxic at 500 mu M, however, not all lipophilic BAs were cytotoxic. Notably, apart from the UDCA primary amide, lipophilic neutral derivatives of UDCA were not cytotoxic. Finally, CDCA, DCA and LagoDCA were prominent outliers being more toxic than predicted by R-Mw. In a hepatic carcinoma line, lipophilicity did not correlate with toxicity except for the common naturally occurring bile acids and their conjugates. There were other significant differences in toxicity between the two cell lines that suggest a possible basis for selective cytotoxicity. The study shows: (i) azido substitution in BAs imparts lipophilicity and toxicity depending on orientation and ionizability; (ii) there is an inverse correlation between R-Mw and toxicity that has good predictive value in homologous sets; (iii) lipophilicity is a necessary but apparently not sufficient characteristic for BA cytocidal activity to which it appears to be indirectly related. (C) 2010 Elsevier Ltd. All rights reserved.
• A convenient synthesis of dinorbile acids:
  作者：Ashok K. Batta、Subhash C. Datta、G.Stephen Tint、David S. Alberts、David L. Earnest、Gerald Salen

  DOI：10.1016/s0039-128x(99)00064-1

  日期：1999.11

  dinorbile acids (23,24-dinor-5beta-cholan-22-oic acids, pregnane-20-carboxylic acids) in fair to good yields from norbile acid nitriles in one step by oxidative hydrolysis with oxygen in the presence of potassium-t-butoxide. The method results in stepwise overall removal of two carbon atoms in bile acid side chains in two steps. Dinorbile acids corresponding to several common bile acids have been prepared

  我们报告了一种简便的方法，可通过氧化水解与一步法从nor酸腈中以合理至良好的产率合成双壬酸（23,24-dinor-5beta-cholan-22-oic酸，pregnane-20-羧酸）叔丁醇钾存在下的氧气。该方法分两步逐步除去胆汁酸侧链中的两个碳原子。已经制备了对应于几种常见胆汁酸的双丁诺酸，并通过光谱法确认了它们的结构。这种简单的合成双降nor酸的方法可能有助于其代谢研究。