1-(1H-indol-3-yl)-2-(4-(pyridin-2-yl)piperazin-1-yl)ethane-1,2-dione | 94254-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(1H-indol-3-yl)-2-(4-(pyridin-2-yl)piperazin-1-yl)ethane-1,2-dione
• 英文别名: 1-(indol-3-yl-oxo-acetyl)-4-pyridin-2-yl-piperazine；1-(1H-indol-3-yl)-2-(4-pyridin-2-ylpiperazin-1-yl)ethane-1,2-dione
• CAS: 94254-78-1
• 化学式: C₁₉H₁₈N₄O₂
• 分子量: 334.378
• InChiKey: YHLDATLLXLFWMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吲哚 以 乙醚 为溶剂， 反应 3.0h， 生成 1-(1H-indol-3-yl)-2-(4-(pyridin-2-yl)piperazin-1-yl)ethane-1,2-dione
  参考文献：
  名称：

  Synthesis and biological activity of novel mono-indole and mono-benzofuran inhibitors of bacterial transcription initiation complex formation

  摘要：

  Our ongoing research focused on targeting transcription initiation in bacteria has resulted in synthesis of several classes of mono-indole and mono-benzofuran inhibitors that targeted the essential protein-protein interaction between RNA polymerase core and sigma(70)/sigma(A) factors in bacteria. In this study, the reaction of indole-2-, indole-3-, indole-7- and benzofuran-2-glyoxyloyl chlorides with amines and hydrazines afforded a variety of glyoxyloylamides and glyoxyloylhydrazides. Similarly, condensation of 2- and 7-trichloroacetylindoles with amines and hydrazines delivered amides and hydrazides. The novel molecules were found to inhibit the RNA polymerase-sigma(70)/sigma(A) interaction as measured by ELISA, and also inhibited the growth of both Gram-positive and Gram-negative bacteria in culture. Structure-activity relationship (SAR) studies of the mono-indole and mono-benzofuran inhibitors suggested that the hydrophilic-hydrophobic balance is an important determinant of biological activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.037

文献信息

• Synthesis and biological activity of novel mono-indole and mono-benzofuran inhibitors of bacterial transcription initiation complex formation
  作者：Marcin Mielczarek、Ruth V. Thomas、Cong Ma、Hakan Kandemir、Xiao Yang、Mohan Bhadbhade、David StC. Black、Renate Griffith、Peter J. Lewis、Naresh Kumar

  DOI：10.1016/j.bmc.2015.02.037

  日期：2015.4

  Our ongoing research focused on targeting transcription initiation in bacteria has resulted in synthesis of several classes of mono-indole and mono-benzofuran inhibitors that targeted the essential protein-protein interaction between RNA polymerase core and sigma(70)/sigma(A) factors in bacteria. In this study, the reaction of indole-2-, indole-3-, indole-7- and benzofuran-2-glyoxyloyl chlorides with amines and hydrazines afforded a variety of glyoxyloylamides and glyoxyloylhydrazides. Similarly, condensation of 2- and 7-trichloroacetylindoles with amines and hydrazines delivered amides and hydrazides. The novel molecules were found to inhibit the RNA polymerase-sigma(70)/sigma(A) interaction as measured by ELISA, and also inhibited the growth of both Gram-positive and Gram-negative bacteria in culture. Structure-activity relationship (SAR) studies of the mono-indole and mono-benzofuran inhibitors suggested that the hydrophilic-hydrophobic balance is an important determinant of biological activity. (C) 2015 Elsevier Ltd. All rights reserved.