24-nor-lithodeoxycholic acid | 4057-91-4

• 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
• 英文名称: 24-nor-lithodeoxycholic acid
• 英文别名: lithocholic acid；24-Norlithocholic acid；3α-hydroxy-24-nor-5β-cholan-23-oic acid；3α-Hydroxy-24-nor-5β-cholan-23-saeure；3α-Hydroxy-24-nor-5β-cholansaeure-(23)；Norlithocholic acid；(3R)-3-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanoic acid
• CAS: 4057-91-4
• 化学式: C₂₃H₃₈O₃
• 分子量: 362.553
• InChiKey: BIGINLZPDKMEPQ-RLEVVIJMSA-N

物化性质

• 熔点：
  183-183.5 °C
• 沸点：
  499.4±18.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  24-nor-lithodeoxycholic acid 在 吡啶 、 palladium hydroxide, 20 wt% on carbon 、 氢气 、 lithium carbonate 、 对甲苯磺酸 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 Methyl-23nor-5β-cholonat
  参考文献：
  名称：

  Investigation on bile acid receptor regulators. Discovery of cholanoic acid derivatives with dual G-protein coupled bile acid receptor 1 (GPBAR1) antagonistic and farnesoid X receptor (FXR) modulatory activity

  摘要：

  Bile acids, the end products of cholesterol metabolism, activate multiple mechanisms through the interaction with membrane G-protein coupled receptors including the bile acid receptor GPBAR1 and nuclear receptors such as the bile acid sensor, farnesoid X receptor (FXR). Even if dual FXR/GPBAR1 agonists are largely considered a novel opportunity in the treatment of several liver and metabolic diseases, selective targeting of one of these receptors represents an attractive therapeutic approach for a wide range of disorders in which dual modulation is associated to severe side effects. In the present study we have investigated around the structure of LCA generating a small library of cholane derivatives, endowed with dual FXR agonism/GPBAR1 antagonism. To the best of our knowledge, this is the first report of bile acid derivatives able to antagonize GPBAR1. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.11.003
• 作为产物：
  描述：

  3α-formyloxy-5β-cholan-24-oic acid 在 三氟乙酸 、 三氟乙酸酐 、 potassium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 24-nor-lithodeoxycholic acid
  参考文献：
  名称：

  Investigation on bile acid receptor regulators. Discovery of cholanoic acid derivatives with dual G-protein coupled bile acid receptor 1 (GPBAR1) antagonistic and farnesoid X receptor (FXR) modulatory activity

  摘要：

  Bile acids, the end products of cholesterol metabolism, activate multiple mechanisms through the interaction with membrane G-protein coupled receptors including the bile acid receptor GPBAR1 and nuclear receptors such as the bile acid sensor, farnesoid X receptor (FXR). Even if dual FXR/GPBAR1 agonists are largely considered a novel opportunity in the treatment of several liver and metabolic diseases, selective targeting of one of these receptors represents an attractive therapeutic approach for a wide range of disorders in which dual modulation is associated to severe side effects. In the present study we have investigated around the structure of LCA generating a small library of cholane derivatives, endowed with dual FXR agonism/GPBAR1 antagonism. To the best of our knowledge, this is the first report of bile acid derivatives able to antagonize GPBAR1. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.11.003

文献信息

• Ercoli; de Ruggieri, Il Farmaco, scienza e tecnica, 1951, vol. 6, p. 547,555,556
  作者：Ercoli、de Ruggieri

  DOI：——

  日期：——
• Preparation of Phenyl Ketones from Bile Acids¹
  作者：Willard M. Hoehn、Robert Bruce Moffett

  DOI：10.1021/ja01221a014

  日期：1945.5
• Farm-related Factors Influencing the Adoption of Short-rotation Willow Coppice Production Among Swedish Farmers
  作者：Anders Roos、Håkan Rosenqvist、Erik Ling、Bo Hektor

  DOI：10.1080/090647100750014385

  日期：2000.1

  The area of short-rotation willow coppice energy plantations on Swedish farmland increased quickly in the early 1990s because of subsidies for energy crop production, an increased CO2 tax on fossil fuel and an already existing biofuel market in the country. In this study farm-related determinants for the adoption of short-rotation willow coppice production among Swedish farmers are identified and estimated. A Tobit model is applied to cross-sectional data on Swedish farmers in 1995. The results show that the decision to plant willow and the areas planted depend positively on arable land area, forest land area, the area of other land types, leasing out of arable land and tractor ownership. Negative factors an pasture areal tenancy and animal production. Differences in willow growing between ownership types, age groups and geographical regions are also important. The policy implications of the results are discussed.
• The Preparation of the Homologs of 3-Hydroxy-12-ketocholanic Acid
  作者：Erwin Schwenk、Byron Riegel、Robert Bruce Moffett、Elsie Stahl

  DOI：10.1021/ja01244a015

  日期：1943.4
• Abbau der Lithocholsäure zu Ätio-lithocholsäure
  作者：J. Sawlewicz、T. Reichstein

  DOI：10.1002/hlca.193702001137

  日期：——