methyl 3β-amino-7α,12α-dihydroxy-5β-cholan-24-oate hydrochloride | 143435-84-1

• 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 3β-amino-7α,12α-dihydroxy-5β-cholan-24-oate hydrochloride
• CAS: 143435-84-1
• 化学式: C₂₅H₄₃NO₄*ClH
• 分子量: 458.082
• InChiKey: TVDGDSYUBLZLOL-MLVYLNRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  92.78
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3β-amino-7α,12α-dihydroxy-5β-cholan-24-oate hydrochloride 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 96.0h， 生成 3,5-bis(((3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-17-((R)-5-methoxy-5-oxopentan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)carbamoyl)-1-methylpyridin-1-ium iodide
  参考文献：
  名称：

  Synthesis of cholate-based pyridinium receptor and its recognition toward l-tryptophan

  摘要：

  Four cholate-based pyridinium compounds were synthesized and their binding abilities toward unmodified amino acids were investigated by UV spectroscopy and fluorescence emission spectroscopy. Studies revealed that the recognition process involved hydrogen bonding, electrostatic force, and pi-pi interaction. The receptor 4a was found to recognize L-tryptophan specifically, and the complex was studied by H-1 NMR spectroscopy. The receptors 4b and 4c showed very little recognition ability toward L-tryptophan, indicating the important role of the benzyl group at pyridinium ring. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.068
• 作为产物：
  描述：

  methyl 3β-azido-7α,12α-dihydroxy-5β-cholan-24-oate 在 水 、 三苯基膦 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 methyl 3β-amino-7α,12α-dihydroxy-5β-cholan-24-oate hydrochloride
  参考文献：
  名称：

  Synthesis of cholate-based pyridinium receptor and its recognition toward l-tryptophan

  摘要：

  Four cholate-based pyridinium compounds were synthesized and their binding abilities toward unmodified amino acids were investigated by UV spectroscopy and fluorescence emission spectroscopy. Studies revealed that the recognition process involved hydrogen bonding, electrostatic force, and pi-pi interaction. The receptor 4a was found to recognize L-tryptophan specifically, and the complex was studied by H-1 NMR spectroscopy. The receptors 4b and 4c showed very little recognition ability toward L-tryptophan, indicating the important role of the benzyl group at pyridinium ring. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.068

文献信息

• Synthesis of new, UV-photoactive dansyl derivatives for flow cytometric studies on bile acid uptake
  作者：Jana Rohacova、M. Luisa Marin、Alicia Martínez-Romero、José-Enrique O'Connor、M. Jose Gomez-Lechon、M. Teresa Donato、Jose V. Castell、Miguel A. Miranda

  DOI：10.1039/b912134j

  日期：——

  Four new fluorescent derivatives of cholic acid have been synthesized; they incorporate a dansyl moiety at 3α-, 3β-, 7α- or 7β- positions. These cholic acid analogs are UV photoactive and also exhibit green fluorescence. In addition, they have been demonstrated to be suitable for studying the kinetics of bile acid transport by flow cytometry.

  已合成四种新的氟荧光胆酸衍生物；它们在3α-、3β-、7α-或7β-位点上引入了丹酰基团。这些胆酸类类似物具有紫外光光活性，并且表现出绿色荧光。此外，已证明它们适合通过流式细胞术研究胆酸运输的动力学。
• Stereodifferentiation in fluorescence quenching within cholic acid aggregates
  作者：M. Consuelo Cuquerella、Jana Rohacova、M. Luisa Marin、Miguel A. Miranda

  DOI：10.1039/c0cc00176g

  日期：——

  Two cholic acid (ChA) analogues, containing a 4-nitrobenzo-2-oxa-1,3-diazole (NBD) moiety at C-3, were incorporated into ChA aggregates and submitted to fluorescence quenching by the two enantiomers of several tryptophan derivatives. In all cases, a significant stereodifferentiation was observed; the most remarkable effect was found when comparing the 3α and the 3β diastereomers.

  两种胆酸（ChA）类似物的 C-3 位含有一个 4-硝基苯并-2-氧杂-1,3-二唑（NBD）分子，它们被加入到 ChA 聚集体中，并被几种色氨酸衍生物的两种对映体淬灭荧光。在所有情况下，都观察到了明显的立体差异；在比较 3α 和 3β 非对映异构体时，发现了最显著的效果。
• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF ARAMCHOL AND SALTS THEREOF<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION D'ARAMCHOL ET DE SES SELS
  申请人：[en]PHARMAZELL GMBH

  公开号：WO2023227723A1

  公开（公告）日：2023-11-30

  The present invention relates to an improved process for the preparation of Aramchol and its pharmaceutically acceptable salts comprising the reaction of the corresponding 3. beta. -amine compound with a mixed anhydride of arachidic acid (Eicosanoic acid).