6-(bromomethyl)-10-methoxy-7H-pyrido<2,3-c>carbazole | 109056-45-3

• 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-(bromomethyl)-10-methoxy-7H-pyrido<2,3-c>carbazole
• 英文别名: 6-(bromomethyl)-10-methoxy-7H-pyrido[2,3-c]carbazole
• CAS: 109056-45-3
• 化学式: C₁₇H₁₃BrN₂O
• 分子量: 341.207
• InChiKey: OFAJPGVDAHDHDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(bromomethyl)-10-methoxy-7H-pyrido<2,3-c>carbazole 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以35%的产率得到10-methoxy-6-methyl-7H-pyrido<2,3-c>carbazole
  参考文献：
  名称：

  Modulation of the antitumor activity by methyl substitutions in the series of 7H-pyridocarbazole monomers and dimers

  摘要：

  The structure of the dimeric antitumor drug ditercalinium (NSC 366241) [2,2'-([4,4'-bipiperidine]-1,1'-diyldi-2,1-ethanediyl)bis[10 -methoxy-7H-pyrido[4,3-c]carbazolium] tetramethanesulfonate] was modified by introduction of methyl groups in various positions of the aromatic ring. Monomeric analogues with the nitrogen atom of the pyridinic ring in different positions have also been synthesized. Pharmacological properties and DNA interactions of the new compounds are reported. In contrast with the monomeric analogue of ditercalinium, which was inactive, methyl substitutions on the 10-methoxy-7H-pyrido[4,3-c]carbazolium in positions 6 or 7 led to monomers endowed with small but significant activity. As expected, dimerization of the methyl-substituted pyridocarbazoles yielded DNA bisintercalators with affinity slightly higher than that of the unsubstituted parent compounds. These dimers, characterized by a relatively better therapeutic index, have the same mechanism of action as ditercalinium. Otherwise, in monomeric and dimeric series, methyl substitution in position 4 or 5 provided inactive compounds unable to intercalate into DNA. All these results are in agreement with the previously proposed geometry for the complex of ditercalinium with DNA.

  DOI：

  10.1021/jm00394a024
• 作为产物：
  描述：

  6-cyano-10-methoxy-7H-pyrido<2,3-c>carbazole 在 镍 六甲基磷酰三胺 、 氨 、 氢溴酸 、 氢气 、 sodium nitrite 作用下， 以 水 为溶剂， 25.0 ℃ 、1000.0 kPa 条件下， 反应 4.0h， 生成 6-(bromomethyl)-10-methoxy-7H-pyrido<2,3-c>carbazole
  参考文献：
  名称：

  Modulation of the antitumor activity by methyl substitutions in the series of 7H-pyridocarbazole monomers and dimers

  摘要：

  The structure of the dimeric antitumor drug ditercalinium (NSC 366241) [2,2'-([4,4'-bipiperidine]-1,1'-diyldi-2,1-ethanediyl)bis[10 -methoxy-7H-pyrido[4,3-c]carbazolium] tetramethanesulfonate] was modified by introduction of methyl groups in various positions of the aromatic ring. Monomeric analogues with the nitrogen atom of the pyridinic ring in different positions have also been synthesized. Pharmacological properties and DNA interactions of the new compounds are reported. In contrast with the monomeric analogue of ditercalinium, which was inactive, methyl substitutions on the 10-methoxy-7H-pyrido[4,3-c]carbazolium in positions 6 or 7 led to monomers endowed with small but significant activity. As expected, dimerization of the methyl-substituted pyridocarbazoles yielded DNA bisintercalators with affinity slightly higher than that of the unsubstituted parent compounds. These dimers, characterized by a relatively better therapeutic index, have the same mechanism of action as ditercalinium. Otherwise, in monomeric and dimeric series, methyl substitution in position 4 or 5 provided inactive compounds unable to intercalate into DNA. All these results are in agreement with the previously proposed geometry for the complex of ditercalinium with DNA.

  DOI：

  10.1021/jm00394a024

文献信息

• LEON, P.;GARBAY-JAUREGUIBERRY, C.;BARSI, M. C.;LE, PECQ J. B.;ROQUES, B. +, J. MED. CHEM., 30,(1987) N 11, 2074-2080
  作者：LEON, P.、GARBAY-JAUREGUIBERRY, C.、BARSI, M. C.、LE, PECQ J. B.、ROQUES, B. +

  DOI：——

  日期：——