1-deoxy-1,1-bis(3'-indolyl)-D-ribitol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-deoxy-1,1-bis(3'-indolyl)-D-ribitol
• 英文别名: (2R,3S,4S)-5,5-bis(1H-indol-3-yl)pentane-1,2,3,4-tetrol
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: ZOZWBDNYRUURIS-NRSPTQNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  113
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吲哚 、 D-核糖 在 碘 、 溶剂黄146 作用下， 生成 1-deoxy-1,1-bis(3'-indolyl)-D-ribitol
  参考文献：
  名称：

  Bis-Indole Derivatives for Polysaccharide Compositional Analysis and Chiral Resolution of D-, L-Monosaccharides by Ligand Exchange Capillary Electrophoresis Using Borate-Cyclodextrin as a Chiral Selector

  摘要：

  一系列醛基双吲哚衍生物（aldo-BINs）通过醛糖和吲哚在醋酸溶液中的芳香C-烷基化反应制备而成。常见的单糖如葡萄糖、甘露糖、半乳糖、岩藻糖、木糖、鼠李糖、核糖、阿拉伯糖和N-乙酰氨基葡萄糖被顺利衍生化，形成了能吸收紫外线的aldo-BINs。建立了使用毛细管电泳法分离这些新型aldo-BIN衍生物的方法。毛细管电泳条件是在高pH（pH 9.0）下使用硼酸盐缓冲液（100 mM）设定的。检测限评估为25 nM。基于手性配体交换毛细管电泳技术实现了D、L对称的aldo-BINs的对映体分离，采用了改性羟丙基-β-环糊精作为手性选择剂，并在硼酸盐缓冲液的存在下进行。这种醛糖标记方法成功应用于糖类的组成和构象分析，以能快速有效地分析来自药用植物冬虫夏草和胡氏石斛的糖类的组成和构象为例。

  DOI：

  10.3390/molecules16021682

文献信息

• Bis-Indole Derivatives for Polysaccharide Compositional Analysis and Chiral Resolution of D-, L-Monosaccharides by Ligand Exchange Capillary Electrophoresis Using Borate-Cyclodextrin as a Chiral Selector
  作者：Chien-Yuan Kuo、Kuo-Shiang Liao、Yin-Chen Liu、Wen-Bin Yang

  DOI：10.3390/molecules16021682

  日期：——

  A series of aldo-bis-indole derivatives (aldo-BINs) was prepared by aromatic C-alkylation reactions of aldoses and indole in acetic acid solution. Common monosaccharides such as glucose, mannose, galactose, fucose, xylose, rhamnose, ribose, arabinose and N-acetylglucosamine were smoothly derivatized to form the UV absorbing aldo-BINs. The use of a capillary electrophoretic method to separate these novel aldo-BIN derivatives was established. The capillary electrophoresis conditions were set by using borate buffer (100 mM) at high pH (pH 9.0). The limit of determination was assessed to be 25 nM. The enantioseparation of D, L-pairs of aldo-BINs based on chiral ligand-exchange capillary electrophoresis technology was also achieved by using modified hydroxypropyl-β-cyclodextrin as the chiral selector in the presence of borate buffer. This aldose labeling method was applied successfully to the compositional and configurational analysis of saccharides, exemplified by a rapid and efficient method to simultaneously analyze the composition and configuration of saccharides from the medicinal herbs Cordyceps sinensis and Dendrobium huoshanense.

  一系列醛基双吲哚衍生物（aldo-BINs）通过醛糖和吲哚在醋酸溶液中的芳香C-烷基化反应制备而成。常见的单糖如葡萄糖、甘露糖、半乳糖、岩藻糖、木糖、鼠李糖、核糖、阿拉伯糖和N-乙酰氨基葡萄糖被顺利衍生化，形成了能吸收紫外线的aldo-BINs。建立了使用毛细管电泳法分离这些新型aldo-BIN衍生物的方法。毛细管电泳条件是在高pH（pH 9.0）下使用硼酸盐缓冲液（100 mM）设定的。检测限评估为25 nM。基于手性配体交换毛细管电泳技术实现了D、L对称的aldo-BINs的对映体分离，采用了改性羟丙基-β-环糊精作为手性选择剂，并在硼酸盐缓冲液的存在下进行。这种醛糖标记方法成功应用于糖类的组成和构象分析，以能快速有效地分析来自药用植物冬虫夏草和胡氏石斛的糖类的组成和构象为例。
• 一种3,3`-双吲哚基甲烷类的制备方法
  申请人：南京工业大学

  公开号：CN115073351A

  公开（公告）日：2022-09-20

  本发明公开了一种3,3'‑双吲哚基甲烷类化合物的制备方法，其结构通式如下所示： 其制备方法如下：取反应装置，依次加入离子对催化剂Ph3C+[B(C6F5)4]‑、取代的吲哚类化合物式、羰基类化合物式，然后加入溶剂，将反应瓶转移至加热装置中加热，并快速搅拌反应，TLC检测反应完成后，经分离纯化，得相应得目标产物。本发明为绿色、高效、原子经济性高、反应条件较温和以及底物适用范围较广的方法制备，本发明制备方法中所需的催化剂为非金属类型的催化剂，与现有的金属催化的合成方法相比，合成过程更易于纯化，不存在金属残留的问题。
• A mild and environmentally friendly scandium(III) trifluoromethanesulfonate-catalyzed synthesis of bis(3′-indolyl)alkanes and bis(3′-indolyl)-1-deoxyalditols
  作者：Shingo Sato、Toshihiro Sato

  DOI：10.1016/j.carres.2005.07.019

  日期：2005.10

  Bis(3'-indolyl)alkanes and bis(3'-indolyl) derivatives containing a 1-deoxyalditol moiety were synthesized in the presence of 5 mol % of scandium(III) trifluoromethanesulfonate [Sc(OTf)(3)] in CH3CN or EtOH-H2O mixture as a solvent from room temperature to 70 degrees C in good yields (78-97%). (C) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and antibacterial evaluation of 3,3′-diindolylmethane derivatives
  作者：Sutapa Roy、Rahul Gajbhiye、Madhumita Mandal、Churala Pal、Arumugam Meyyapan、Joydeep Mukherjee、Parasuraman Jaisankar

  DOI：10.1007/s00044-013-0737-7

  日期：2014.3

  Various 3,3'-diindolylmethane (DIM) derivatives were synthesized and the antibacterial activity of these compounds were tested against ten bacterial strains and their minimum inhibitory concentration (MIC) values were determined. The MIC values of derivatives 3a-d and 5a-e were ranging from 125 to 500 mu g/mL. Among these derivatives, 2-(di(1H-indol-3-yl)methyl)phenol (5a) and 3-((1H-indol-3-yl)(pyridin-3-yl)methyl)-1H-indole (5d) exhibited potent activity, showing MIC values 6.5-62.5 mu g/mL against Gram positive and Gram negative bacteria. Hemolytic assay of these active DIM derivatives did not show considerable toxic effect on the normal human erythrocytes.