5-phenylquinoline-8-carboxylic acid | 113431-49-5

• 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: 5-phenylquinoline-8-carboxylic acid
• CAS: 113431-49-5
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: KCKXUFIUWNJGJH-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  449.7±33.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲基乙二胺 、 5-phenylquinoline-8-carboxylic acid 在 N,N'-羰基二咪唑 作用下， 生成 N-[2-(二甲氨基)乙基]-5-苯基喹啉-8-甲酰胺盐酸(1:1)
  参考文献：
  名称：

  Potential antitumor agents. 56. Minimal DNA-intercalating ligands as antitumor drugs: phenylquinoline-8-carboxamides

  摘要：

  A series of isomeric phenylquinoline-8-carboxamides have been synthesized and evaluated as antitumor agents. This configuration is close to the minimum chromophore required for intercalative binding, since the binding mode of the compounds is dependent on the presence and position of the phenyl ring. If the ring is appended at the 4- or 5-position, it cannot lie within the DNA-intercalation site, and the compounds do not intercalate as shown by both unwinding and helix extension assays. In contrast, the 2-, 3-, and 6-phenyl isomers (where the phenyl ring lies coplanar with the quinoline and in the intercalation site) bind by intercalation. Only those isomers that intercalate show in vivo antitumor activity, with the 2-phenyl derivative in particular possessing broad-spectrum activity in both leukemia and solid-tumor assays.

  DOI：

  10.1021/jm00400a029
• 作为产物：
  描述：

  8-methyl-5-phenylquinoline 在 selenium(IV) oxide 作用下， 生成 5-phenylquinoline-8-carboxylic acid
  参考文献：
  名称：

  Potential antitumor agents. 56. Minimal DNA-intercalating ligands as antitumor drugs: phenylquinoline-8-carboxamides

  摘要：

  A series of isomeric phenylquinoline-8-carboxamides have been synthesized and evaluated as antitumor agents. This configuration is close to the minimum chromophore required for intercalative binding, since the binding mode of the compounds is dependent on the presence and position of the phenyl ring. If the ring is appended at the 4- or 5-position, it cannot lie within the DNA-intercalation site, and the compounds do not intercalate as shown by both unwinding and helix extension assays. In contrast, the 2-, 3-, and 6-phenyl isomers (where the phenyl ring lies coplanar with the quinoline and in the intercalation site) bind by intercalation. Only those isomers that intercalate show in vivo antitumor activity, with the 2-phenyl derivative in particular possessing broad-spectrum activity in both leukemia and solid-tumor assays.

  DOI：

  10.1021/jm00400a029

文献信息

• ATWELL, GRAHAM J.;BOS, CLAUDIA D.;BAGULEY, BRUCE C.;DENNY, WILLIAM A., J. MED. CHEM., 31,(1988) N 5, 1048-1052
  作者：ATWELL, GRAHAM J.、BOS, CLAUDIA D.、BAGULEY, BRUCE C.、DENNY, WILLIAM A.

  DOI：——

  日期：——
• Potential antitumor agents. 56. Minimal DNA-intercalating ligands as antitumor drugs: phenylquinoline-8-carboxamides
  作者：Graham J. Atwell、Claudia D. Bos、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00400a029

  日期：1988.5

  A series of isomeric phenylquinoline-8-carboxamides have been synthesized and evaluated as antitumor agents. This configuration is close to the minimum chromophore required for intercalative binding, since the binding mode of the compounds is dependent on the presence and position of the phenyl ring. If the ring is appended at the 4- or 5-position, it cannot lie within the DNA-intercalation site, and the compounds do not intercalate as shown by both unwinding and helix extension assays. In contrast, the 2-, 3-, and 6-phenyl isomers (where the phenyl ring lies coplanar with the quinoline and in the intercalation site) bind by intercalation. Only those isomers that intercalate show in vivo antitumor activity, with the 2-phenyl derivative in particular possessing broad-spectrum activity in both leukemia and solid-tumor assays.