3α,7α,12α-trihydroxy-5β-cholan-24-(2-dimethylaminoethyl)amide | 140674-57-3

• 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: 3α,7α,12α-trihydroxy-5β-cholan-24-(2-dimethylaminoethyl)amide
• 英文别名: N-(2-dimethylaminoethyl)cholamide；(4R)-N-[2-(dimethylamino)ethyl]-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanamide
• CAS: 140674-57-3
• 化学式: C₂₈H₅₀N₂O₄
• 分子量: 478.716
• InChiKey: WLQBSXOUVHVQMP-SREHDYERSA-N

物化性质

• 熔点：
  159-162 °C
• 沸点：
  646.9±55.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  93
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-碘己烷 、 3α,7α,12α-trihydroxy-5β-cholan-24-(2-dimethylaminoethyl)amide 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 以91%的产率得到3-cholanamidoethylhexyldimethylammonium iodide
  参考文献：
  名称：

  [EN] COMPOUND FOR TREATING CLOSTRIDIUM DIFFICILE
  [FR] COMPOSÉ DESTINÉ AU TRAITEMENT CONTRE CLOSTRIDIUM DIFFICILE

  摘要：

  这项发明涉及包含第一成分的化合物、组合物和聚合物，该第一成分适用于促进厌氧梭菌（C.diff）的萌发，并包含作为抗菌剂的第二成分。所述化合物、组合物和聚合物可用于在传统抗菌剂无效的情况下销毁C.diff。这些组合物可以制成涂层或材料的形式，主动破坏与其接触的C.diff。胆盐诱导促进萌发。该发明还涉及将这类材料用作治疗C.diff相关疾病和毒性巨结肠的用途。

  公开号：

  WO2016083819A1
• 作为产物：
  描述：

  胆酸 在 4-二甲氨基吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 37.08h， 生成 3α,7α,12α-trihydroxy-5β-cholan-24-(2-dimethylaminoethyl)amide
  参考文献：
  名称：

  Structure and Dynamics of a Molecular Hydrogel Derived from a Tripodal Cholamide

  摘要：

  Tripodal cholamide 1 is a supergelator of aqueous fluids. A variety of physical techniques, including cryo-transmission electron microscopy (TEM), circular dichroism (CD), steady-state fluorescence, time-resolved fluorescence, and dynamic light-scattering, were employed to understand the structure and dynamics of the gel. Fluorescent probes [ANS (8-anilinonaphthalene-1-sulfonic acid) and pyrene] reported two critical aggregation concentrations (CAC(1) and CAC(2)) of 1 in predominantly aqueous media, with the minimum gel concentration (MGC) being close to CAC(2). Fluorescence lifetime measurements with pyrene revealed ineffective quenching of pyrene fluorescence by oxygen, possibly caused by slower Brownian diffusion due to the enhanced viscosity in the gel phase. The study of the gelation kinetics by monitoring the ultrafast dynamics of ANS revealed a progressive increase in the aggregate size and the microviscosity of the aqueous pool encompassed by the self-assembled fibrillar network (SAFIN) during the gelation. The striking difference between microviscosity and bulk (macroscopic) viscosity of the gel is also discussed.

  DOI：

  10.1021/ja046788t

文献信息

• Polarity-Tuning Derivatization-LC-MS Approach for Probing Global Carboxyl-Containing Metabolites in Colorectal Cancer
  作者：Xiqing Bian、Na Li、Binbin Tan、Baoqing Sun、Ming-Quan Guo、Guoxin Huang、Li Fu、W. L. Wendy Hsiao、Liang Liu、Jian-Lin Wu

  DOI：10.1021/acs.analchem.8b01873

  日期：2018.10.2

  Carboxyl-containing metabolites (CCMs) widely exist in living systems and are the essential components for life. Global characteristics of CCMs in biological samples are critical for the understanding of physiological processes and the discovery for the onset of relevant diseases. However, their determination represents a challenge due to enormous polarity differences, structural diversity, high structural similarity, and poor ionization efficiency in mass spectrometry. Herein, 5-(diisopropylamino)amylamine (DIAAA) derivatization coupled with liquid chromatography–mass spectrometry (LC-MS) was developed for mapping the CCMs. With this methodology, the sensitivity was significantly enhanced. More importantly, the hydrophobicity of polar CCMs, amino acids, TCA cycle intermediates, and short-chain fatty acids and the hydrophilicity of low-polar CCMs, long-chain fatty acids, and bile acids were significantly increased, resulting in a remarkable separation efficiency for which 68 CCMs can be simultaneously determined. Furthermore, the polarity-tuning effect was confirmed to be induced by the different impacts of aliphatic chains and nitrogen atom in DIAAA, the latter existing as a cation in the acidic mobile phase, using different derivatization reagents. Finally, this derivatization method was utilized to hunt for the potential biomarkers in colorectal cancer (CRC) patients and 52 CCMs, related with several key metabolic pathways, including amino acids metabolism, TCA cycle, fatty acid metabolism, pyruvate metabolism, and gut flora metabolism were identified. This innovative polarity-tuning derivatization-LC-MS approach was proved to be a valuable tool for probing global metabolome with high separation efficiency and sensitivity in various biological samples.

  含羧基代谢物（CCMs）广泛存在于生物系统中，是生命的基本组成部分。CCMs在生物样本中的全球特征对于理解生理过程和发现相关疾病的发生具有重要意义。然而，由于极性差异巨大、结构多样性、高结构相似性和在质谱中的离子化效率较低，它们的测定面临挑战。在此，我们开发了5-(二异丙基氨基)戊胺（DIAAA）衍生化结合液相色谱-质谱（LC-MS）的方法以绘制CCMs的分布。通过这种方法，灵敏度显著提高。更重要的是，极性CCMs、氨基酸、TCA循环中间体和短链脂肪酸的疏水性显著增强，而低极性CCMs、长链脂肪酸和胆汁酸的亲水性也显著增加，从而实现了卓越的分离效率，使得68种CCMs可以同时测定。此外，极性调节效应被证实是由于DIAAA中脂肪链和氮原子的不同影响所引起的，后者在酸性流动相中以阳离子的形式存在，使用不同的衍生化试剂。最后，该衍生化方法被用于寻找结直肠癌（CRC）患者的潜在生物标志物，识别出52种与多条关键代谢通路（包括氨基酸代谢、TCA循环、脂肪酸代谢、丙酮酸代谢和肠道菌群代谢）相关的CCMs。这种创新的极性调节衍生化-LC-MS方法被证明是探测各种生物样本全球代谢组的高分离效率和灵敏度的有价值工具。
• Novel bile acid conjugates with aryl/alkenyl linker: Synthesis and characterization
  作者：Juha Koivukorpi、Erkki Kolehmainen

  DOI：10.1016/j.molstruc.2008.01.050

  日期：2008.10

  Abstract Eight potential precursors for the design of bile acid derived receptors viz. 2,6-bis[dimethyl(3α-hydroxy-5β-cholan-24-amidoethyl)ammonio-methyl]naphthalene dibromide (1), 3,3′-bis[dimethyl(3α-hydroxy-5β-cholan-24-amidoethyl)ammoniomethyl]biphenyl dibromide (2), 3,3′-bis[dimethyl(3α,7α,12α-trihydroxy-5β-cholan-24-amidoethyl)ammoniomethyl]biphenyl dibromide (3), 4,4′-bis[dimethyl(3α-hydrox

  摘要 胆汁酸衍生受体设计的八种潜在前体，即。2,6-双[二甲基(3α-羟基-5β-cholan-24-酰胺乙基)氨甲基]萘二溴化物 (1), 3,3'-双[二甲基(3α-羟基-5β-cholan-24-酰胺乙基) )氨甲基]联苯二溴化物 (2), 3,3'-双[二甲基(3α,7α,12α-三羟基-5β-cholan-24-酰胺乙基)氨甲基]联苯二溴化物 (3), 4,4'-双[二甲基(3α-hydroxy-5β-cholan-24-amidoethyl)ammoniomethyl]stilbene dibromide (4), 4,4'-bis[dimethyl(3α,7α,12α-trihydroxy-5β-cholan-24-amidoethyl)ammoniomethyl]stilbene dibromide (5)、烯丙基-二甲基(3α,7α,12α-trihydroxy-5β-c
• Design, synthesis and spectral studies of novel bile acid-arene conjugates: Trans to cis isomerization of azobenzene core controlled by bile acid hydrophobicity
  作者：Juha Koivukorpi、Erkki Kolehmainen

  DOI：10.1016/j.molstruc.2007.03.058

  日期：2008.3

  Four bile acid-arene conjugates, 1,4-bis[dimethyl(3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cliolan-24-amidoethyl)ammoniomethyl]benzene dibromide (1), 1,3,5-tris[dimetliyl(3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholan-24-amidoethyl)ammoniomethyl]benzene tribromide (2), bis4-[dimethyl-(3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholan-24-amidoethyl)ammoniomethyl]phenyl}diazene dibromide (3), and bis4-[dimethyl(3 alpha-hydroxy-5 beta-cholan-24-amidoethyl)ammoniomethyl]phenyl}diazene dibromide (4), have been synthesized in good yields, and their structures have been characterized by H-1, C-13, C-13 DEPT-135, PFG H-1, C-13 HMQC, PFG H-1, C-13 HMBC, and PFG H-1, N-15 HMBC NMR spectra. Their molecular weights and elemental compositions have been determined by ESI-TOF mass spectrometry and elemental analyses. Trans to cis isomerization of azobenzene derivatives 3 and 4 have also been studied. It was found that by increasing the hydrophobicity of bile acid moiety (from cholyl to lithocholyl) the trans to cis photoinduced isomerization tendency is increased in a protic solvent. (C) 2007 Elsevier B.V. All rights reserved.
• COMPOUND FOR TREATING CLOSTRIDIUM DIFFICILE
  申请人：Aston University

  公开号：EP3223855A1

  公开（公告）日：2017-10-04