N-(2-(1H-indol-3-yl)ethyl)-N-methyl-2-nitrobenzenesulfonamide | 1004321-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-(1H-indol-3-yl)ethyl)-N-methyl-2-nitrobenzenesulfonamide
• CAS: 1004321-65-6
• 化学式: C₁₇H₁₇N₃O₄S
• 分子量: 359.406
• InChiKey: PNHUWXRBFKNPBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96.31
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)-N-methyl-2-nitrobenzenesulfonamide 在 N-溴代丁二酰亚胺(NBS) 、 甲酸 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 生成 2-(6-bromo-1-butyl-1H-indol-3-yl)-N-methylethan-1-amine
  参考文献：
  名称：

  Intercepting Bacterial Indole Signaling with Flustramine Derivatives

  摘要：

  Indole signaling is one of the putative universal signaling networks in bacteria. We have investigated the use of desformylflustrabromine (dFBr) derivatives for the inhibition of biofilm formation through modulation of the indole-signaling network in Escherichia coli and Staphylococcus aureus. We have found dFBr derivatives that are 10-1000 times more active than indole itself, demonstrating that the flustramine family of indolic natural products represent a privileged scaffold for the design of molecules to control pathogenic bacterial behavior.

  DOI：

  10.1021/ja209836z
• 作为产物：
  描述：

  色胺 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(2-(1H-indol-3-yl)ethyl)-N-methyl-2-nitrobenzenesulfonamide
  参考文献：
  名称：

  Intercepting Bacterial Indole Signaling with Flustramine Derivatives

  摘要：

  Indole signaling is one of the putative universal signaling networks in bacteria. We have investigated the use of desformylflustrabromine (dFBr) derivatives for the inhibition of biofilm formation through modulation of the indole-signaling network in Escherichia coli and Staphylococcus aureus. We have found dFBr derivatives that are 10-1000 times more active than indole itself, demonstrating that the flustramine family of indolic natural products represent a privileged scaffold for the design of molecules to control pathogenic bacterial behavior.

  DOI：

  10.1021/ja209836z

文献信息

• First Total Synthesis of Trimeric Indole Alkaloid, Psychotrimine
  作者：Yohei Matsuda、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1021/ol702637r

  日期：2008.1.1

  The first total synthesis of (+/-)-psychotrimine, a novel trimeric indole alkaloid isolated from Psychotria rostrata, was achieved. In the total synthesis, the copper-mediated intramolecular and intermolecular aminations of halobenzenes, which respectively contributed to the construction of a pyrrolidinoindoline core and the installation of a third tryptamine unit, were used as key steps.

  实现了（+/-）-Psychotrimine的首次全合成，这是一种从Psychotria rostrata分离的新型三聚吲哚生物碱。在整个合成过程中，关键步骤采用了铜介导的卤代苯的分子内和分子间胺化反应，这些胺化反应分别构成了吡咯烷基二氢吲哚核的构造和第三个色胺单元的安装。
• Determination of absolute configuration of trimeric indole alkaloid, psychotrimine, by first asymmetric total synthesis
  作者：Nobuaki Takahashi、Takeshi Ito、Yohei Matsuda、Noriyuki Kogure、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1039/b923918a

  日期：——

  The first asymmetric total synthesis of psychotrimine, a trimeric indole alkaloid, was accomplished via an asymmetric Ireland-Claisen rearrangement to construct a chiral quaternary carbon center, thereby establishing the absolute configuration of psychotrimine.

  精神三胺（三聚吲哚生物碱）的第一个不对称全合成是通过不对称的Ireland-Claisen重排完成的，以构建手性季碳中心，从而建立了精神三胺的绝对构型。