1-(2-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetyl)-N-(2-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)ethyl)pyrrolidine-2-carboxamide | 1146685-21-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetyl)-N-(2-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)ethyl)pyrrolidine-2-carboxamide
• 英文别名: KCB4-199
• CAS: 1146685-21-3
• 化学式: C₂₇H₂₈N₆O₄S₂
• 分子量: 564.689
• InChiKey: RJPYAVLKHWRSCK-MIFGFRIJSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114.75
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(2-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetyl)-N-(2-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)ethyl)pyrrolidine-2-carboxamide 、 丁香醛 在 哌啶 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 17.0h， 以11 mg的产率得到1-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetyl)-N-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)ethyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Tethered thiazolidinone dimers as inhibitors of the bacterial type III secretion system

  摘要：

  Disruption of protein-protein interactions by small molecules is achievable but presents significant hurdles for effective compound design. In earlier work we identified a series of thiazolidinone inhibitors of the bacterial type III secretion system (T3SS) and demonstrated that this scaffold had the potential to be expanded into molecules with broad-spectrum anti-Gram negative activity. We now report on one series of thiazolidinone analogs in which the heterocycle is presented as a dimer at the termini of a series of linkers. Many of these dimers inhibited the T3SS-dependent secretion of a virulence protein at concentrations lower than that of the original monomeric compound identified in our screen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.047
• 作为产物：
  描述：

  1-(2-(3-phenylthioureido)acetyl)-N-(2-(3-phenylthioureido)oethyl)pyrrolidine-2-carboxamide 、 溴乙酸甲酯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以150 mg的产率得到1-(2-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetyl)-N-(2-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)ethyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Tethered thiazolidinone dimers as inhibitors of the bacterial type III secretion system

  摘要：

  Disruption of protein-protein interactions by small molecules is achievable but presents significant hurdles for effective compound design. In earlier work we identified a series of thiazolidinone inhibitors of the bacterial type III secretion system (T3SS) and demonstrated that this scaffold had the potential to be expanded into molecules with broad-spectrum anti-Gram negative activity. We now report on one series of thiazolidinone analogs in which the heterocycle is presented as a dimer at the termini of a series of linkers. Many of these dimers inhibited the T3SS-dependent secretion of a virulence protein at concentrations lower than that of the original monomeric compound identified in our screen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.047