(S)-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamido)-N-(3-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)propyl)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanamide | 1146685-12-2

• 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: (S)-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamido)-N-(3-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)propyl)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanamide
• 英文别名: KCB4-053
• CAS: 1146685-12-2
• 化学式: C₆₀H₆₇N₉O₁₃S₃
• 分子量: 1218.44
• InChiKey: HDMZFWRILINNGR-BATPPUEESA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  85.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  292.2
• 氢给体数：
  7.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamido)-N-(3-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)propyl)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanamide 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 2.0h， 以1.6 mg的产率得到(S)-5-guanidino-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamido)-N-(3-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)propyl)pentanamide trifluoroacetate
  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：

  (S)-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamido)-N-(3-((Z)-4-oxo-2-(phenylimino)thiazolidin-3-yl)propyl)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanamide 、 丁香醛 在 哌啶 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 以8.7 mg的产率得到(S)-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamido)-N-(3-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)propyl)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanamide
  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