(-)-(2R)-2-methoxy-2-(2'-β-D-thioglucopyranosyl-1'H-indol-3'-yl)acetonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2R)-2-methoxy-2-(2'-β-D-thioglucopyranosyl-1'H-indol-3'-yl)acetonitrile
• 英文别名: isatindigotindoloside C
• 化学式: C₁₇H₂₀N₂O₆S
• 分子量: 380.422
• InChiKey: HTKAGWRREBZANX-CJBGRTLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  138.96
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (-)-(2R)-2-methoxy-2-(2'-β-D-thioglucopyranosyl-1'H-indol-3'-yl)acetonitrile 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 葡萄糖
  参考文献：
  名称：

  Indole alkaloid glucosides from the roots of Isatis indigotica

  摘要：

  Five new indole alkaloid glucosides named isatindigotindolosides A-E (1-5), along with three known analogs (6-8), were isolated from an aqueous extract of the Isatis indigotica roots. Their structures including the absolute configurations were determined based on comprehensive spectroscopic data analysis, combined with chemical methods and electronic circular dichroism spectra calculations. In the preliminary assays, compounds 1, 6 and 7 showed antiviral activity against influenza virus A/Hanfang/359/95 (H3N2) with IC50 values of 14.6-33.3 mu M. Compound 1 also exhibited inhibitory effect against nitric oxide (NO) production in microglial cell BV2 with an inhibition ratio of 93.0% at 10 mu M.

  DOI：

  10.1080/10286020.2015.1117452

文献信息

• Indole alkaloid glucosides from the roots of <i>Isatis indigotica</i>
  作者：Yu-Feng Liu、Ming-Hua Chen、Sheng Lin、Yu-Huan Li、Dan Zhang、Jian-Dong Jiang、Jian-Gong Shi

  DOI：10.1080/10286020.2015.1117452

  日期：2016.1.2

  Five new indole alkaloid glucosides named isatindigotindolosides A-E (1-5), along with three known analogs (6-8), were isolated from an aqueous extract of the Isatis indigotica roots. Their structures including the absolute configurations were determined based on comprehensive spectroscopic data analysis, combined with chemical methods and electronic circular dichroism spectra calculations. In the preliminary assays, compounds 1, 6 and 7 showed antiviral activity against influenza virus A/Hanfang/359/95 (H3N2) with IC50 values of 14.6-33.3 mu M. Compound 1 also exhibited inhibitory effect against nitric oxide (NO) production in microglial cell BV2 with an inhibition ratio of 93.0% at 10 mu M.