9-(2-Methoxy-phenylamino)-phenazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide | 875714-20-8

• 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: 9-(2-Methoxy-phenylamino)-phenazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide
• CAS: 875714-20-8
• 化学式: C₂₄H₂₅N₅O₂
• 分子量: 415.495
• InChiKey: TZSCOHLSSKSXHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  79.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  9-(2-Methoxy-phenylamino)-phenazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以24%的产率得到
  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：

  9-fluorophenazine-1-carboxylic acid 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 9-(2-Methoxy-phenylamino)-phenazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide
  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