methyl 3α-azido-12α-hydroxy-5β-cholan-24-oate | 403607-37-4

• 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: methyl 3α-azido-12α-hydroxy-5β-cholan-24-oate
• 英文别名: methyl (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-azido-12-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]pentanoate
• CAS: 403607-37-4
• 化学式: C₂₅H₄₁N₃O₃
• 分子量: 431.619
• InChiKey: ZZLPBWPJJAQPCQ-JMKDMENQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3α-azido-12α-hydroxy-5β-cholan-24-oate 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以90%的产率得到(3α,5β,12α)-3-amino-12-hydroxycholan-24-oic acid methyl ester
  参考文献：
  名称：

  手性金属-有机笼中构象变化和配位体氢键的影响

  摘要：

  我们报道了由甾体胆酸与Pd（II）离子合成形成手性金属-有机Pd 2（1）4笼的手性双吡啶基配体（1）的协调驱动自组装。胆酸的烷基链中有利的构象变化促进了笼的自组装。DFT研究表明，配体氢键在指导不同可能异构体之间C 4对称笼的形成中起着至关重要的作用，正如DFT研究和使用不同配体的对照实验所表明的那样。

  DOI：

  10.1021/acs.inorgchem.8b03610
• 作为产物：
  描述：

  去氧胆酸 在 4-二甲氨基吡啶 、 sodium azide 、 偶氮二甲酸二异丙酯 、 硫酸 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 methyl 3α-azido-12α-hydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  手性金属-有机笼中构象变化和配位体氢键的影响

  摘要：

  我们报道了由甾体胆酸与Pd（II）离子合成形成手性金属-有机Pd 2（1）4笼的手性双吡啶基配体（1）的协调驱动自组装。胆酸的烷基链中有利的构象变化促进了笼的自组装。DFT研究表明，配体氢键在指导不同可能异构体之间C 4对称笼的形成中起着至关重要的作用，正如DFT研究和使用不同配体的对照实验所表明的那样。

  DOI：

  10.1021/acs.inorgchem.8b03610

文献信息

• Tripodal Bile Acid Architectures Based on a Triarylphosphine Oxide Core Obtained by Copper-Catalysed [1,3]-Dipolar Cycloaddition: Synthesis and Preliminary Aggregation Studies
  作者：Bala N. S. Thota、Aramballi J. Savyasachi、Nikolay Lukashev、Irina Beletskaya、Uday Maitra

  DOI：10.1002/ejoc.201301443

  日期：2014.3

  We report the synthesis and aggregation behaviour of new water-soluble, bile acid derived tripodal architectures based on a core derived from triphenylphosphine oxide. We employed the well-established copper-catalysed [1,3]-dipolar cycloaddition (CuAAC) for the construction of these tripodal molecules. The aggregation behaviour of these molecules in aqueous media was studied by different analytical

  我们报告了基于衍生自氧化三苯基膦的核心的新型水溶性、胆汁酸衍生的三足结构的合成和聚集行为。我们采用成熟的铜催化 [1,3]-偶极环加成 (CuAAC) 来构建这些三足分子。这些分子在水性介质中的聚集行为通过不同的分析方法进行研究，例如染料增溶、动态光散射、核磁共振和原子力显微镜。这些分子结构还提供了额外的优势，有助于理解胆汁酸骨架的性质和这些结构中类固醇 C-3 位置的构型的影响；据我们所知，这在文献中还没有报道。
• Synthesis of Bile Acid Dimers Linked with 1,2,3-Triazole Ring at C-3, C-11, and C-24 Positions
  作者：Vandana S. Pore、Nilkanth G. Aher

  DOI：10.1055/s-2005-872223

  日期：——

  1,3-Dipolar cycloaddition of propargyl ester of a bile acid to an azide group attached at different positions of another bile acid gave three new 1,2,3-triazole-containing dimeric analogues in excellent yields.

  将一种胆汁酸的丙炔基酯与另一种胆汁酸不同位置上的叠氮基进行 1,3-二极环加成，得到了三种新的含 1,2,3-三唑的二聚类似物，产量极高。
• New fluorescent bile acids: Synthesis, chemical characterization, and disastereoselective uptake by Caco-2 cells of 3-deoxy 3-NBD-amino deoxycholic and ursodeoxycholic acid
  作者：Ferenc Májer、Johanna J. Salomon、Ruchika Sharma、Simona V. Etzbach、Mohd Nadzri Mohd Najib、Ray Keaveny、Aideen Long、Jun Wang、Carsten Ehrhardt、John F. Gilmer

  DOI：10.1016/j.bmc.2012.01.002

  日期：2012.3

  Deoxycholic acid (DCA), a secondary bile acid (BA), and ursodeoxycholic acid (UDCA), a tertiary BA, cause opposing effects in vivo and in cell suspensions. Fluorescent analogues of DCA and UDCA could help investigate important questions about their cellular interactions and distribution.We have prepared a set of isomeric 3 alpha- and 3 beta-amino analogues of UDCA and DCA and derivatised these with the discrete fluorophore, 4-nitrobenzo-2-oxa-1,3-diazol (NBD), forming the corresponding four fluorescent adducts. These absorb in the range 465-470 nm and fluoresce at approx. 535 nm.In order to determine the ability of the new fluorescent bile acids to mimic the parents, their uptake was studied using monolayers of Caco-2 cells, which are known to express multiple proteins of the organic anion-transporting peptide (OATP) subfamily of transporters. Cellular uptake was monitored over time at 4 and 37 degrees C to distinguish between passive and active transport.All four BA analogues were taken up but in a strikingly stereo-and structure-specific manner, suggesting highly discriminatory interactions with transporter protein(s). The alpha-analogues of DCA and to a lesser extent UDCA were actively transported, whereas the beta-analogues were not. The active transport process was saturable, with Michaelis-Menten constants for 3 alpha-NBD DCA (5) being K-m = 42.27 +/- 12.98 mu M and V-max = 2.8 +/- 0.4 nmol/(mg protein*min) and for 3 alpha-NBD UDCA (3) K-m = 28.20 +/- 7.45 mu M and V-max = 1.8 +/- 0.2 nmol/(mg protein(*)min). These fluorescent bile acids are promising agents for investigating questions of bile acid biology and for detection of bile acids and related organic anion transport processes. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, synthesis, and micellar properties of bile acid dimers and oligomers linked with a 1,2,3-triazole ring
  作者：Nilkanth G. Aher、Vandana S. Pore、Sachin P. Patil

  DOI：10.1016/j.tet.2007.10.042

  日期：2007.12

  1,3-Dipolar cycloaddition of propargyl esters of bile acids to azide group attached at different positions of bile acids gave dimers, trimer, and tetramer linked with 1,2,3-triazole. These dimeric and oligomeric structures were able to solubilize hydrophilic dye-cresol red, in nonpolar solvent. (c) 2007 Elsevier Ltd. All rights reserved.
• Scale-Up of Trisodium [(3β,5β,12α)-3-[[4(<i>S</i>)-4-[Bis[2-[bis[(carboxy-<i>kO</i>)methyl]amino-<i>kN</i>]ethyl]amino-<i>kN</i>]-4-(carboxy-<i>kO</i>)-1-oxobutyl]amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography
  作者：Pier Lucio Anelli、Marino Brocchetta、Luciano Lattuada、Giuseppe Manfredi、Pierfrancesco Morosini、Marcella Murru、Daniela Palano、Marco Sipioni、Massimo Visigalli

  DOI：10.1021/op900008a

  日期：2009.7.17

  Process chemistry involved in the discovery and development routes to trisodium [(3 beta,5 beta,12(alpha)-3-[[4(S)-4-[bis[2-[bis[(carboxy-kO)methyl]amino-kN]ethyl]amino-kN]4-(carboxy-kO)-1-oxobutyl]- amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)] (B22956/1) starting from L-glutamic acid and (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid is described. The best process is based on seven chemical steps and overcomes difficult purification protocols. Such process has been successfully implemented to prepare multikilogram batches of the target compound in 20% overall yield from (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid.