tris(2-hydroxyethyl)ammonium 1-benzylindol-3-ylsulfanylacetate | 728041-68-7

• 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: tris(2-hydroxyethyl)ammonium 1-benzylindol-3-ylsulfanylacetate
• 英文别名: 2-hydroxy-N,N-bis(2-hydroxyethyl)ethaneammonium [(1-benzylindol-3-yl)sulfanyl]acetate；2-(1-Benzylindol-3-yl)sulfanylacetate;tris(2-hydroxyethyl)azanium
• CAS: 728041-68-7
• 化学式: C₆H₁₅NO₃*C₁₇H₁₅NO₂S
• 分子量: 446.568
• InChiKey: IKWFOUXWGGZSDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-苄基吲哚 在 hydrazine hydrate 、 碘 、 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 17.0h， 生成 tris(2-hydroxyethyl)ammonium 1-benzylindol-3-ylsulfanylacetate
  参考文献：
  名称：

  1-R-吲哚-3-基硫烷基（磺酰基）烷烃羧酸（2-羟乙基）铵盐的定向合成和免疫活性特性

  摘要：

  从合成 1-烷基（烯丙基）（苄基）-取代的（吲哚-3-基）-硫烷基烷烃羧酸和己烷-1,6-二基（1,4-亚苯基亚甲基）双吲哚-3-基硫烷基烷烃羧酸的一般方法相应的 N 取代吲哚和双吲哚、硫脲、碘和卤代羧酸被开发出来。取代的 (indol-3-yl) 硫烷基烷羧酸首次氧化得到含有磺酰基的类似物。合成了新的 (2-羟乙基) 铵盐 1-R-indol-3-ylsulfanyl(sulfonyl)-alkanechair 酸，它们是吲哚胺和 VILIM 的高活性免疫调节剂的结构类似物。在所研究的 1-R-吲哚-3-基硫基乙酸和-磺酰基烷烃羧酸的（2-羟乙基）铵盐中，

  DOI：

  10.1007/s11172-010-0384-9

文献信息

• Immunoactive ionic liquids based on 2-hydroxyethylamines and 1-R-indol-3-ylsulfanylacetic acids. Crystal and molecular structure of immunodepressant tris-(2-hydroxyethyl)ammonium indol-3-ylsulfanylacetate
  作者：Anna N. Mirskova、Sergey N. Adamovich、Rudolf G. Mirskov、Olga P. Kolesnikova、Uwe Schilde

  DOI：10.1515/chem-2015-0018

  日期：2015.12.31

  Immunoactive ionic liquids (2-hydroxyethyl)ammonium 1-R-indol-3-ylsulfanyl-acetates HN+R1R2(CH2CH2OH) ∙ -O(O)CCH2S-Ind-R3-1 (1-5), were synthesized by the reaction of (2-hydroxyethyl)amines with indol-3-ylsulfanylacetic- or 1-benzylindol-3-ylsulfanylacetic acid. 1: R₁ = R₂ = CH₂CH₂OH, R₃ = H; 2: R₁ = СН₃,R₂=CH₂CH₂OH, R₃ = H; 3: R₁ = R₂ = CH₃, R₃ = H; 4: R₁ = R₂ = CH₂CH₂OH, R₃ = СH₂С₆Н₅; 5: R₁ = СН₃; R₂ = CH₂CH₂OH; R₃ = СH₂С₆Н₅. The structure of each compound was elucidated by IR, NMR ¹H, ¹³С, and ¹⁵N techniques and their composition was confirmed by elemental analysis. The crystal structure of tris-(2-hydroxyethyl) ammonium indol-3-ylsulfanylacetate was investigated by X-ray diffraction analysis. Immunoactive properties of the title compounds were screened.

  通过(2-羟乙基)胺与吲哚-3-基硫酸乙酯或1-苄基吲哚-3-基硫酸乙酯反应，合成了免疫活性离子液体(2-羟乙基)氨基酸1-R-吲哚-3-基硫酰乙酸盐 HN+R1R2(CH2CH2OH) ∙ -O(O)CCH2S-Ind-R3-1 (1-5)。其中，1: R₁ = R₂ = CH₂CH₂OH，R₃ = H；2: R₁ = СН₃，R₂=CH₂CH₂OH，R₃ = H；3: R₁ = R₂ = CH₃，R₃ = H；4: R₁ = R₂ = CH₂CH₂OH，R₃ = СH₂С₆Н₅；5: R₁ = СН₃；R₂ = CH₂CH₂OH；R₃ = СH₂С₆Н₅。采用红外光谱、核磁共振技术(¹H、¹³С、¹⁵N)和元素分析确定了每个化合物的结构和组成。采用X射线衍射分析研究了三(2-羟乙基)氨基酸吲哚-3-基硫酰乙酸盐的晶体结构。对所述化合物的免疫活性进行了筛选。

• Synthesis of Immunoactive Tris(2-hydroxyethyl)ammonium 1-R-Indol-3-ylsulfanyl(sulfonyl)acetates
  作者：S. N. Adamovich、A. N. Mirskova

  DOI：10.1134/s1070427218030205

  日期：2018.3

  Difficultly accessible 1-R-indol-3-ylsulfanyl(sulfonyl)acetic acids 1-R-IndYCH(2)CO(2)H (R = H, Me, Bn; Y = S, SO2) 1a-Id were prepared. Their reaction with tris(2-hydroxyethyl)amine yielded tris(2-hydroxyethyl) ammonium 1-R-indol-3-ylsulfanyl(sulfonyl)aceetates (protatranes) 2a-2d. The immunoactive properties of 2a-2d were studied. Protatranes 2a, 2c, and 2d proved to be effective immunosuppressive agents (up to 99.5% inhibition of mice splenocyte proliferation in vitro).
• Directed synthesis and immunoactive properties of (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)alkanecarboxylic acids
  作者：A. N. Mirskova、G. G. Levkovskaya、O. P. Kolesnikova、O. M. Perminova、E. V. Rudyakova、S. N. Adamovich

  DOI：10.1007/s11172-010-0384-9

  日期：2010.12

  for the first time afforded their analogs containing the sulfonyl group. New (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)-alkanecarboxylic acids, which are structural analogs of highly active immunomodulators of indacetamin and VILIM, were synthesized. Among the studied (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanylacetic and -sulfonylalkanecarboxylic acids, the compounds

  从合成 1-烷基（烯丙基）（苄基）-取代的（吲哚-3-基）-硫烷基烷烃羧酸和己烷-1,6-二基（1,4-亚苯基亚甲基）双吲哚-3-基硫烷基烷烃羧酸的一般方法相应的 N 取代吲哚和双吲哚、硫脲、碘和卤代羧酸被开发出来。取代的 (indol-3-yl) 硫烷基烷羧酸首次氧化得到含有磺酰基的类似物。合成了新的 (2-羟乙基) 铵盐 1-R-indol-3-ylsulfanyl(sulfonyl)-alkanechair 酸，它们是吲哚胺和 VILIM 的高活性免疫调节剂的结构类似物。在所研究的 1-R-吲哚-3-基硫基乙酸和-磺酰基烷烃羧酸的（2-羟乙基）铵盐中，