(E,Z)-2-imino-1-methyl-5-((5-(1-oxo-1,3-dihydroisobenzofuran-5-yl)thiophen-2-yl)methylene)imidazolidin-4-one | 1313397-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (E,Z)-2-imino-1-methyl-5-((5-(1-oxo-1,3-dihydroisobenzofuran-5-yl)thiophen-2-yl)methylene)imidazolidin-4-one
• 英文别名: 2-amino-1-methyl-5-[[5-(1-oxo-3H-2-benzofuran-5-yl)thiophen-2-yl]methylidene]imidazol-4-one
• CAS: 1313397-09-9
• 化学式: C₁₇H₁₃N₃O₃S
• 分子量: 339.375
• InChiKey: ZQGFYLIYUNWDCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(5-溴-2-噻吩基)-1,3-二氧戊环 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 水 、 sodium carbonate 、 溶剂黄146 、 β-丙氨酸 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 20.0h， 生成 (E,Z)-2-imino-1-methyl-5-((5-(1-oxo-1,3-dihydroisobenzofuran-5-yl)thiophen-2-yl)methylene)imidazolidin-4-one
  参考文献：
  名称：

  Inhibition of the pore-forming protein perforin by a series of aryl-substituted isobenzofuran-1(3H)-ones

  摘要：

  An aryl-substituted isobenzofuran-1(3H)-one lead compound was identified from a high throughput screen designed to find inhibitors of the lymphocyte pore-forming protein perforin. A series of analogs were then designed and prepared, exploring structure-activity relationships through variation of 2-thioxoimidazolidin-4-one and furan subunits on an isobenzofuranone core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perforin protein and perforin delivered in situ by intact KHYG-1 natural killer effector cells was determined. Several compounds showed excellent activity at concentrations that were non-toxic to the killer cells. This series represents a significant improvement on previous classes of compounds, being substantially more potent and largely retaining activity in the presence of serum. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.011

文献信息

• Inhibition of the pore-forming protein perforin by a series of aryl-substituted isobenzofuran-1(3H)-ones
  作者：Julie A. Spicer、Kristiina M. Huttunen、Christian K. Miller、William A. Denny、Annette Ciccone、Kylie A. Browne、Joseph A. Trapani

  DOI：10.1016/j.bmc.2011.12.011

  日期：2012.2

  An aryl-substituted isobenzofuran-1(3H)-one lead compound was identified from a high throughput screen designed to find inhibitors of the lymphocyte pore-forming protein perforin. A series of analogs were then designed and prepared, exploring structure-activity relationships through variation of 2-thioxoimidazolidin-4-one and furan subunits on an isobenzofuranone core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perforin protein and perforin delivered in situ by intact KHYG-1 natural killer effector cells was determined. Several compounds showed excellent activity at concentrations that were non-toxic to the killer cells. This series represents a significant improvement on previous classes of compounds, being substantially more potent and largely retaining activity in the presence of serum. (C) 2011 Elsevier Ltd. All rights reserved.