N-(6-nitrobenzo[d]thiazol-2-yl)-2-((3,4,5-trimethoxyphenyl)amino)nicotinamide | 1531604-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-(6-nitrobenzo[d]thiazol-2-yl)-2-((3,4,5-trimethoxyphenyl)amino)nicotinamide
• CAS: 1531604-31-5
• 化学式: C₂₂H₁₉N₅O₆S
• 分子量: 481.489
• InChiKey: REYUIOCXTZUURW-UHFFFAOYSA-N

物化性质

• 密度：
  1.466±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  137.74
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-(6-nitrobenzo[d]thiazol-2-yl)-2-((3,4,5-trimethoxyphenyl)amino)nicotinamide 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以80%的产率得到3-(6-nitrobenzo[d]thiazol-2-yl)-1-(3,4,5-trimethoxyphenyl)-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one
  参考文献：
  名称：

  Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers

  摘要：

  A series of benzothiazole linked phenylpyridopyrimidinones (8a-g) and their diones (9a-g) have been designed, synthesized and evaluated for their anticancer activity. Among the series one of the conjugate 8b showed significant cytotoxicity against human cervical cancer cell line ME-180 with IC50 value of 4.01 mu M. This compound was tested on the cell cycle perturbations and DNA damage. Flow cytometry analysis revealed that the compound 8b showed drastic cell cycle perturbations due to concentration dependent increase in the sub-G0 phase in ME-180 cell line. DNA fragmentation and Hoechst staining reveals that this compound induced cell death by apoptosis. Further caspase-3 and loss of mitochondrial membrane potential suggested that the compound induces cell death by apoptosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.057
• 作为产物：
  描述：

  2-氯烟酸 在 硫酸 、 1-羟基苯并三唑 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 N-(6-nitrobenzo[d]thiazol-2-yl)-2-((3,4,5-trimethoxyphenyl)amino)nicotinamide
  参考文献：
  名称：

  Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers

  摘要：

  A series of benzothiazole linked phenylpyridopyrimidinones (8a-g) and their diones (9a-g) have been designed, synthesized and evaluated for their anticancer activity. Among the series one of the conjugate 8b showed significant cytotoxicity against human cervical cancer cell line ME-180 with IC50 value of 4.01 mu M. This compound was tested on the cell cycle perturbations and DNA damage. Flow cytometry analysis revealed that the compound 8b showed drastic cell cycle perturbations due to concentration dependent increase in the sub-G0 phase in ME-180 cell line. DNA fragmentation and Hoechst staining reveals that this compound induced cell death by apoptosis. Further caspase-3 and loss of mitochondrial membrane potential suggested that the compound induces cell death by apoptosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.057