2-<(dimethylamino)methyl>-5-methoxyindole methiodide | 62099-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-<(dimethylamino)methyl>-5-methoxyindole methiodide
• 英文别名: 5-methoxy-2-<(dimethylamino)methyl>indole methiodide；5-methoxy-2-[(dimethylamino)methyl]indole methiodide；(5-Methoxy-1H-indol-2-yl)-N,N,N-trimethylmethanaminium iodide；(5-methoxy-1H-indol-2-yl)methyl-trimethylazanium;iodide
• CAS: 62099-67-6
• 化学式: C₁₃H₁₉N₂O*I
• 分子量: 346.211
• InChiKey: SLRQZYMJUJPQDS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<(dimethylamino)methyl>-5-methoxyindole methiodide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 2-(5-metoxyindol-2-yl)-3-(3-pyridyl)acrylonitrile
  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

• DNA intercalating compounds as potential antitumor agents. 1. Preparation and properties of 7H-pyridocarbazoles
  作者：Didier Pelaprat、Robert Oberlin、Irene Le Guen、Jean Bernard Le Pecq、Bernard P. Roques

  DOI：10.1021/jm00186a009

  日期：1980.12

  The DNA intercalating compounds derived from 6H-pyridocarbazole (ellipticines, olivacines) elicit high antitumor properties. In order to get information about the mechanism of action of these agents it is necessary to study structurally related analogues. For this purpose, various derivatives of the four isomeric 7H-pyridocarbazoles were synthesized by a single photochemical process on indolylpyridylethylenes. These derivatives are able to intercalate into DNA. The DNA binding affinities vary in the range of 10(4) to 10(6) M-1, depending mainly on the nature of the substituent, nitrogen quaternization being the most enhancing factor. The position of the pyridinic nitrogen does not markedly affect the DNA binding affinity. Three quaternized compounds elicit a significative but low antileukemic activity on L1210 mice leukemia. The properties of 7H-pyridocarbazoles are discussed and compared to those of 6H-pyridocarbazoles (ellipticines and olivacines).
• 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：——
• Modulation of the antitumor activity by methyl substitutions in the series of 7H-pyridocarbazole monomers and dimers
  作者：P. Leon、C. Garbay-Jaureguiberry、M. C. Barsi、J. B. Le Pecq、Bernard P. Roques

  DOI：10.1021/jm00394a024

  日期：1987.11

  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.