1-甲氧基-3-(2-硝基乙烯基)吲哚 | 69111-76-8

• 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
• 中文名称: 1-甲氧基-3-(2-硝基乙烯基)吲哚
• 英文名称: 1-methoxy-3-(2-nitrovinyl)indole
• 英文别名: 3-(2-nitrovinyl)-1-methoxyindole；1-Methoxy-3-(2-nitrovinyl)indol；1-Methoxy-3-(2-nitroethenyl)-1H-indole；1-methoxy-3-(2-nitroethenyl)indole
• CAS: 69111-76-8
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: MLYPCEODUGJFFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲氧基-3-(2-硝基乙烯基)吲哚 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 乙酸酐 为溶剂， 生成 N_b-formyl-1-methoxytryptamine
  参考文献：
  名称：

  Somei, Masanori; Sato, Haruhiko; Komura, Naoko, Heterocycles, 1985, vol. 23, # 5, p. 1101 - 1106

  摘要：

  DOI：
• 作为产物：
  描述：

  1-羟基吲哚 在 ammonium acetate 、 甲基三辛基氯化铵 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醚 、 水 为溶剂， 反应 26.0h， 生成 1-甲氧基-3-(2-硝基乙烯基)吲哚
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of indole glucosinolates

  摘要：

  The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassicin (NGB) in moderate overall yield for the first time. The anti-inflammatory activity of the synthetic indole GLs was determined by inhibition of TNF-alpha secretion in LPS-stimulated THP-1 cells. The data showed that glucobrassicin (GB) exhibited higher activity than other synthetic indolyl GLs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.003

文献信息

• Synthesis of aromatic and indole alpha-glucosinolates
  作者：Quan V. Vo、Simone Rochfort、Pham C. Nam、Tuan L. Nguyen、Trung T. Nguyen、Adam Mechler

  DOI：10.1016/j.carres.2017.11.004

  日期：2018.1

  α-glucosinolates are also promising compounds for medicinal applications and hence have to be produced synthetically for any bio-activity studies. Here we report on the successful synthesis of a series of α-glucosinolates: α-neoglucobrassicin, α-4-methoxyglucobrassicin, 2,3-dichlorophenyl-α-glucosinolate for the first time. Testing for anti-inflammatory properties of these synthetic GLs, however, did not yield

  就其潜在的医学特性而言，芳族和吲哚芥子油苷是化合物芥子油苷家族的重要成员。已知它们通过天然产物本身或它们的代谢产物（包括吲哚-3-甲醇和异硫氰酸酯）发挥抗氧化和抗癌活性。天然的芥子油苷都是β-芥子油苷。然而，α-芥子油苷也是用于医学应用的有前途的化合物，因此对于任何生物活性研究都必须合成生产。在这里，我们首次报道了一系列α-芥子油苷的成功合成：α-新葡糖苷，α-4-甲氧基葡糖苷，2,3-二氯苯基-α-芥子油苷。但是，这些合成GL的抗炎特性测试并未产生预期的活性。
• Synthesis and anti-inflammatory activity of indole glucosinolates
  作者：Quan V. Vo、Craige Trenerry、Simone Rochfort、Jenny Wadeson、Carolina Leyton、Andrew B. Hughes

  DOI：10.1016/j.bmc.2013.12.003

  日期：2014.1

  The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassicin (NGB) in moderate overall yield for the first time. The anti-inflammatory activity of the synthetic indole GLs was determined by inhibition of TNF-alpha secretion in LPS-stimulated THP-1 cells. The data showed that glucobrassicin (GB) exhibited higher activity than other synthetic indolyl GLs. (C) 2013 Elsevier Ltd. All rights reserved.
• Somei, Masanori; Sato, Haruhiko; Komura, Naoko, Heterocycles, 1985, vol. 23, # 5, p. 1101 - 1106
  作者：Somei, Masanori、Sato, Haruhiko、Komura, Naoko、Kaneko, Chikara

  DOI：——

  日期：——