3α-formyloxy-5β-cholan-24-oic acid | 5015-59-8

• 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: 3α-formyloxy-5β-cholan-24-oic acid
• 英文别名: 3α-O-formyllithocholic acid；3alpha-Formyloxy-5beta-cholan-24-oic acid；(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-formyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 5015-59-8
• 化学式: C₂₅H₄₀O₄
• 分子量: 404.59
• InChiKey: PBSOPSDEYNTFAZ-ULCLHEGSSA-N

物化性质

• 熔点：
  142 °C
• 沸点：
  516.4±19.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3α-formyloxy-5β-cholan-24-oic acid 在 三氟乙酸 、 三氟乙酸酐 、 sodium nitrite 作用下， 反应 4.0h， 以380 mg的产率得到3α-formyloxy-24-nor-5β-cholan-23-nitrile
  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：

  石胆酸 在 高氯酸 、 乙酸酐 作用下， 以 甲酸 、 水 为溶剂， 生成 3α-formyloxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Chemical synthesis

  摘要：

  这项发明涉及具有D环侧链结构的类固醇化合物，其化学式为，其中R.sub.1可以是或--C.sub.n H.sub.2n --，其中n是从0到8的整数；Y可以是S、N或O；x是1到3的整数；每个Z可以相同也可以不同，选自H、OH、烷基、芳基、芳基烷基、酰氧基、环烷基、取代烷基、取代芳基或取代环烷基的基团。

  公开号：

  US04460509A1

文献信息

• Mehrwertige Alkohole aus Sterinen und Sterinderivaten, VI Steroide mit Strukturmerkmalen des Ecdysons und der Elatericine
  作者：Hans Lettré、Jürgen Greiner、Klaus Rutz、Lothar Hofmann、Alfons Egle、Wilfried Bieger

  DOI：10.1002/jlac.19727580109

  日期：1972.7.12

  Aus Litho-, Desoxy- und Chenodesoxycholsäure (1a – c) wurden über die Homosäuren 5a – c die tert.-C25-Carbinole 7a – c dargestellt. Cholesterin ließ sich in das Ecdyson-analoge Produkt 18b umwandeln. Hyodesoxy- und Homohyodesoxycholsäure wurden in die Tetrole 33a, b übergeführt. Aus 34a – d wurden die Steroide 37a – d mit diosphenolischer Struktur gewonnen.

  AUS Litho-，Desoxy- UNDChenodesoxycholsäure（1A - C ^）wurden黚死Homosäuren 5A - Ç模具叔-C 25 -Carbinole 7A - Ç dargestellt。位于Das Ecdyson-Analoge Produkt 18b umwandeln中的胆固醇。Hyodesoxy- UNDHomohyodesoxycholsäurewurden裸片Tetrole部33a，b übergeführt。Aus 34a – d沸腾的硬脂酸酯37a – d mit diosphenolischer Struktur gewonnen。
• Steroid and bile acids amide conjugates with D-glucosamine
  作者：Zdena Nováková、Jana Tomanová、Lucie Štěrbová、Pavel Drašar

  DOI：10.1135/cccc2010105

  日期：——

  New type of amide conjugates of steroid and bile acids with D-glucosamine 1 and 2 were prepared. Title compounds are prepared via acid chloride or using N-[([(1E)-1-cyano-2-ethoxy-2-oxoethylidene]amino}oxy)(dimethylamino)methylidene]-N-methylmethanaminium tetrafluoroborate as condensation agent. They were examined for gelation properties with negative results. Per-O-acetylated D-glucosamine hydrochloride was prepared in one step procedure from D-glucosamine hydrochloride by acetylation in a mixture of acetyl chloride and acetic acid.

  新型酰胺共轭物，包括类固醇和胆汁酸与D-葡萄糖胺1和2，已经制备。标题化合物是通过酸氯化物或使用N-[([(1E)-1-氰基-2-乙氧基-2-氧基乙基]氨基氧}(二甲氨基)甲基亚甲基]-N-甲基甲胺四氟硼酸盐作为缩聚剂制备的。它们被检查了凝胶化性能，结果为阴性。经过过氧化的D-葡萄糖胺盐酸盐通过在乙酸氯和乙酸混合物中乙酰化一步法从D-葡萄糖胺盐酸盐制备而成。
• Protonation and deprotonation induced organo/hydrogelation: Bile acid derived gelators containing a basic side chain
  作者：Uday Maitra、Arkajyoti Chakrabarty

  DOI：10.3762/bjoc.7.40

  日期：——

  Two bile acid derived molecules containing basic amino groups are reported to be efficient and unusual gelators of organic and aqueous solvents.

  报道称，两种含有碱性氨基的胆汁酸衍生分子被证明是有效且不同寻常的有机溶剂和水溶剂凝胶剂。
• Perfluoroalkyl bile esters: a new class of efficient gelators of organic and aqueous–organic media
  作者：Supratim Banerjee、V. M. Vidya、A. J. Savyasachi、Uday Maitra

  DOI：10.1039/c1jm11912e

  日期：——

  A new class of fluorinated gelators derived from bile acids is reported. Perfluoroalkyl chains were attached to the bile acids through two different ester linkages and were synthesized following simple transformations. The gelation property of these derivatives is a function of the bile acid moiety, the spacer and the fluoroalkyl chain length. By varying these parameters, gels were obtained in aromatic hydrocarbons, DMSO and DMSO/DMF–H2O mixtures of different proportions. Several derivatives of deoxycholic and lithocholic acids were found to be efficient organogelators, while the reported bile-acid based organogelators are mostly derived from the cholic acid moiety. The efficient gelators among these compounds formed gels well below 1.0% (w/v) and hence they can be termed as supergelators. The mechanical properties of these gels could be modulated by changing either the bile acid moiety or by varying the length of the fluoroalkyl segment. The presence of CO2-philic perfluoroalkyl groups is also expected to enhance their solubility in supercritical CO2 and hence these compounds are promising candidates for making aerogels.

  报告了一类源自胆汁酸的新型氟化凝胶剂。全氟烷基链通过两种不同的酯键连接到胆汁酸，经过简单转化合成。这些衍生物的凝胶性能取决于胆汁酸部分、间隔链和氟烷基链的长度。通过改变这些参数，可以在芳香烃、DMSO以及不同比例的DMSO/DMF-H2O混合物中获得凝胶。发现几种脱氧胆酸和石胆酸的衍生物是高效的有机凝胶剂，而现有的基于胆汁酸的有机凝胶剂大多源于胆酸部分。这些化合物中高效的凝胶剂在低于1.0%（w/v）的浓度下即可形成凝胶，因此可以称之为超凝胶剂。通过改变胆汁酸部分或氟烷基段的长度，可以调节这些凝胶的机械性能。CO₂亲和的全氟烷基团的存在也预计将增强其在超临界CO₂中的溶解度，因此这些化合物在制作气凝胶方面具有很大的潜力。
• Long-acting contraceptive agents: Bile acid esters of norethisterone
  作者：J.E. Herza、J. Sandoval

  DOI：10.1016/0039-128x(83)90103-4

  日期：1983.3

  The synthesis of the esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) with three bile acids and of the cholesteryl carbonate of norethisterone are described.

  描述了炔诺酮 (17 α-ethynyl-17 beta-hydroxyestr-4-en-3-one) 与三种胆汁酸的酯的合成和炔诺酮的胆甾醇碳酸酯的合成。