3H-9-chloro-1-formyl-pyrrolo[3,2-f]quinoline | 288570-19-4

• 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: 3H-9-chloro-1-formyl-pyrrolo[3,2-f]quinoline
• 英文别名: 9-chloro-3H-pyrrolo[3,2-f]quinoline-1-carbaldehyde
• CAS: 288570-19-4
• 化学式: C₁₂H₇ClN₂O
• 分子量: 230.653
• InChiKey: SLCDSLKFDCTHKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.75
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-甲磺酰胺基苯胺 、 3H-9-chloro-1-formyl-pyrrolo[3,2-f]quinoline 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以50%的产率得到N-[4-(3,7,12-triazatetracyclo[6.5.2.04,15.011,14]pentadeca-1(13),4(15),5,7,9,11(14)-hexaen-3-yl)phenyl]methanesulfonamide;hydrochloride
  参考文献：
  名称：

  Pyrrolo-quinoline derivatives as potential antineoplastic drugs

  摘要：

  Some novel pyrrolo-quinoline derivatives have been synthesized as potential antineoplastic agents. They contain an angular aromatic tricyclic or tetracyclic system, to which the methanesulfon-anisidide side chain typical of amsacrine as such, or lacking the m-methoxy substituent, is connected. A methyl group can be present at position 7 of the pyrrolo-quinoline ring. The novel compounds exhibit interesting cell growth inhibitory properties when tested against the NCI panel of cell lines, in particular those obtained from solid tumors like CNS-, melanoma- and prostate-derived cells. The mechanism of cytotoxic action does not seem to be related to topoisomerase II poisoning ability. Most active proved to be compound 4a, which lacks both methyl and methoxy substituents, followed by 5a, having the methoxy group only. Biological activity is less pronounced in the tetracyclic family of derivatives 6 and 7. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00060-2
• 作为产物：
  描述：

  diethyl 2-[(1H-indol-5-ylamino)methylidene]propanedioate 在 sodium hydroxide 、 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 2.83h， 生成 3H-9-chloro-1-formyl-pyrrolo[3,2-f]quinoline
  参考文献：
  名称：

  Pyrrolo-quinoline derivatives as potential antineoplastic drugs

  摘要：

  Some novel pyrrolo-quinoline derivatives have been synthesized as potential antineoplastic agents. They contain an angular aromatic tricyclic or tetracyclic system, to which the methanesulfon-anisidide side chain typical of amsacrine as such, or lacking the m-methoxy substituent, is connected. A methyl group can be present at position 7 of the pyrrolo-quinoline ring. The novel compounds exhibit interesting cell growth inhibitory properties when tested against the NCI panel of cell lines, in particular those obtained from solid tumors like CNS-, melanoma- and prostate-derived cells. The mechanism of cytotoxic action does not seem to be related to topoisomerase II poisoning ability. Most active proved to be compound 4a, which lacks both methyl and methoxy substituents, followed by 5a, having the methoxy group only. Biological activity is less pronounced in the tetracyclic family of derivatives 6 and 7. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00060-2