| 942268-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• CAS: 942268-02-2
• 化学式: C₁₄H₁₉N₅S
• 分子量: 289.404
• InChiKey: QTYGBKSDOYEGAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.24
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  、 5-(2-Bromoprop-2-enoylamino)-1-benzothiophene-2-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-(2-bromoprop-2-enoylamino)-N-[6-([1,2,4]thiadiazolo[4,5-a]benzimidazol-1-ylamino)hexyl]-1-benzothiophene-2-carboxamide
  参考文献：
  名称：

  Hybrid molecules containing benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole and α-bromoacryloyl moieties as potent apoptosis inducers on human myeloid leukaemia cells

  摘要：

  The synthesis and biological activity of a series of hybrids 1-5 prepared combining a benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole and different benzoheterocyclic alpha-bromoacryloyl amides have been described and their structure-activity relationships discussed. All these hetero-bifunctional compounds were highly cytotoxic against the human myeloid leukaemia cell lines HL-60 and U937 (IC50 0.24-1.72 mu M), significantly superior to that of both alkylating units alone. In human myeloid leukaemia HL-60 cells we observed that these compounds suppress survival and proliferation by triggering morphological changes and internucleosomal DNA fragmentation characteristic of apoptotic cell death. The apoptosis induced by these compounds is mediated by caspase-3 activation and is also associated to an early release of cytochrome c from the mitochondria. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.048
• 作为产物：
  描述：

  3-(toluene-4-sulfonyl)-benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole 、 1,6-己二胺 在 TEA 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Hybrid molecules containing benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole and α-bromoacryloyl moieties as potent apoptosis inducers on human myeloid leukaemia cells

  摘要：

  The synthesis and biological activity of a series of hybrids 1-5 prepared combining a benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole and different benzoheterocyclic alpha-bromoacryloyl amides have been described and their structure-activity relationships discussed. All these hetero-bifunctional compounds were highly cytotoxic against the human myeloid leukaemia cell lines HL-60 and U937 (IC50 0.24-1.72 mu M), significantly superior to that of both alkylating units alone. In human myeloid leukaemia HL-60 cells we observed that these compounds suppress survival and proliferation by triggering morphological changes and internucleosomal DNA fragmentation characteristic of apoptotic cell death. The apoptosis induced by these compounds is mediated by caspase-3 activation and is also associated to an early release of cytochrome c from the mitochondria. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.048