6-(4-chlorophenyl)-N-(2-(dimethylamino)ethyl)phenanthridine-4-carboxamide | 112421-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(4-chlorophenyl)-N-(2-(dimethylamino)ethyl)phenanthridine-4-carboxamide
• 英文别名: 6-(4-chlorophenyl)-N-[2-(dimethylamino)ethyl]phenanthridine-4-carboxamide
• CAS: 112421-89-3
• 化学式: C₂₄H₂₂ClN₃O
• 分子量: 403.911
• InChiKey: HGXOYXWBGLKLTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-2-硝基苯胺 在 chromium(VI) oxide 、 盐酸 、 PPA 、 硫酸 、 potassium acetate 、 氢气 、 铁粉 、 N,N'-羰基二咪唑 、 sodium nitrite 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 6-(4-chlorophenyl)-N-(2-(dimethylamino)ethyl)phenanthridine-4-carboxamide
  参考文献：
  名称：

  Potential antitumor agents. 55. 6-Phenylphenanthridine-4-carboxamides: a new class of DNA-intercalating antitumor agents

  摘要：

  Derivatives of the DNA-intercalating agent N-[2-(dimethylamino)ethyl]phenanthridine-4-carboxamide have been prepared and shown to have moderate in vivo antitumor activity against both the P388 leukemia and Lewis lung carcinoma. This demonstrates that the effective pharmacophore in the broad class of tricyclic carboxamides is not limited to linear tricyclic chromophores. Both 7 and the 6-phenyl derivative 10 have identical DNA binding properties, suggesting that the phenyl ring of 10 is not involved in the DNA intercalation site. A series of phenyl-substituted derivatives of 10 was evaluated. Aza substituents led to compounds with the highest in vivo cytotoxicity and in vivo P388 activity, but the in vivo solid tumor activity of the substituted 6-phenylphenanthridine-4-carboxamides was in general low.

  DOI：

  10.1021/jm00399a015

文献信息

• Modular Synthesis of Phenanthridine Derivatives by Oxidative Cyclization of 2-Isocyanobiphenyls with Organoboron Reagents
  作者：Mamoru Tobisu、Keika Koh、Takayuki Furukawa、Naoto Chatani

  DOI：10.1002/anie.201206115

  日期：2012.11.5

  Where HAS you been? A manganese‐mediated annulation of 2‐isocyanobiaryls with organoboronic acids is developed for the synthesis of a broad range of phenanthridine derivatives (see scheme). Mechanistic studies indicate that the reaction proceeds by the intramolecular homolytic aromatic substitution (HAS) of an imidoyl radical intermediate.

  你去哪了 开发了锰介导的2-异氰基联芳基与有机硼酸的环合反应，用于合成广泛的菲啶衍生物（请参见方案）。机理研究表明，该反应通过亚氨基自由基中间体的分子内均溶芳族取代（HAS）进行。
• ATWELL, GRAHAM J.;BAGULEY, BRUCE C.;DENNY, WILLIAM A., J. MED. CHEM., 31,(1988) N 4, 774-779
  作者：ATWELL, GRAHAM J.、BAGULEY, BRUCE C.、DENNY, WILLIAM A.

  DOI：——

  日期：——
• Potential antitumor agents. 55. 6-Phenylphenanthridine-4-carboxamides: a new class of DNA-intercalating antitumor agents
  作者：Graham J. Atwell、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00399a015

  日期：1988.4

  Derivatives of the DNA-intercalating agent N-[2-(dimethylamino)ethyl]phenanthridine-4-carboxamide have been prepared and shown to have moderate in vivo antitumor activity against both the P388 leukemia and Lewis lung carcinoma. This demonstrates that the effective pharmacophore in the broad class of tricyclic carboxamides is not limited to linear tricyclic chromophores. Both 7 and the 6-phenyl derivative 10 have identical DNA binding properties, suggesting that the phenyl ring of 10 is not involved in the DNA intercalation site. A series of phenyl-substituted derivatives of 10 was evaluated. Aza substituents led to compounds with the highest in vivo cytotoxicity and in vivo P388 activity, but the in vivo solid tumor activity of the substituted 6-phenylphenanthridine-4-carboxamides was in general low.