N-(8,9-benzophenazin-1-yl)-2-bromoacetamide | 875714-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(8,9-benzophenazin-1-yl)-2-bromoacetamide
• 英文别名: N-benzo[a]phenazin-11-yl-2-bromoacetamide
• CAS: 875714-35-5
• 化学式: C₁₈H₁₂BrN₃O
• 分子量: 366.217
• InChiKey: FQEWHPQGAIVZMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.88
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(8,9-benzophenazin-1-yl)-2-bromoacetamide 、 二甲胺 以 乙醇 为溶剂， 以99%的产率得到N-benzo[a]phenazin-11-yl-2-(dimethylamino)acetamide
  参考文献：
  名称：

  Phenazine-1-carboxamides: Structure–cytotoxicity relationships for 9-substituents and changes in the H-bonding pattern of the cationic side chain

  摘要：

  A series of phenazine-1-carboxamides were prepared, including variations in both chromophore substituents and the nature of the cationic side chain. The novel side-chain analogues were prepared from the corresponding phenazine-1-carboxylic acids via Schmidt conversion to the 1-amines and from the corresponding 1-halides. Structure-cytotoxicity relationships for these compounds in a panel of tumor cell lines showed that there is very limited scope for variation of the structure of the 1-carboxamide side chain, consistent with the recent Structural model of flow tricyclic carboxamides bind to DNA. There was generally little difference in IC(50)s between parent and P-glycoprotein expressing cell lines, suggesting that most of the compounds are not affected by the presence of this efflux pump. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.032
• 作为产物：
  描述：

  benzophenazine-11-carboxylic acid 在 sodium azide 、 PPA 作用下， 以 二氯甲烷 为溶剂， 反应 4.33h， 生成 N-(8,9-benzophenazin-1-yl)-2-bromoacetamide
  参考文献：
  名称：

  Phenazine-1-carboxamides: Structure–cytotoxicity relationships for 9-substituents and changes in the H-bonding pattern of the cationic side chain

  摘要：

  A series of phenazine-1-carboxamides were prepared, including variations in both chromophore substituents and the nature of the cationic side chain. The novel side-chain analogues were prepared from the corresponding phenazine-1-carboxylic acids via Schmidt conversion to the 1-amines and from the corresponding 1-halides. Structure-cytotoxicity relationships for these compounds in a panel of tumor cell lines showed that there is very limited scope for variation of the structure of the 1-carboxamide side chain, consistent with the recent Structural model of flow tricyclic carboxamides bind to DNA. There was generally little difference in IC(50)s between parent and P-glycoprotein expressing cell lines, suggesting that most of the compounds are not affected by the presence of this efflux pump. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.032