(S,Z)-(9H-fluoren-9-yl)methyl 1-oxo-1-(3-(4-oxo-2-(phenylimino)thiazolidin-3-yl)propylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentan-2-ylcarbamate | 1146685-10-0

• 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,Z)-(9H-fluoren-9-yl)methyl 1-oxo-1-(3-(4-oxo-2-(phenylimino)thiazolidin-3-yl)propylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentan-2-ylcarbamate
• 英文别名: KCB4-041
• CAS: 1146685-10-0
• 化学式: C₄₆H₅₃N₇O₇S₂
• 分子量: 880.102
• InChiKey: MGXGVOIPUCKBNS-PYGRFLHSSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  62.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  191.38
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S,Z)-(9H-fluoren-9-yl)methyl 1-oxo-1-(3-(4-oxo-2-(phenylimino)thiazolidin-3-yl)propylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentan-2-ylcarbamate 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以324 mg的产率得到(S,Z)-2-amino-N-(3-(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
• 作为产物：
  描述：

  (Z)-3-(3-aminopropyl)-2-(phenylimino)thiazolidin-4-one 、 Fmoc-Pbf-L-精氨酸 在 N,N'-羰基二咪唑 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以526 mg的产率得到(S,Z)-(9H-fluoren-9-yl)methyl 1-oxo-1-(3-(4-oxo-2-(phenylimino)thiazolidin-3-yl)propylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentan-2-ylcarbamate
  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