2-chloro-8-methoxy-11H-indolo[3,2-c]quinoline

• 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: 2-chloro-8-methoxy-11H-indolo[3,2-c]quinoline
• 化学式: C₁₆H₁₁ClN₂O
• 分子量: 282.729
• InChiKey: SNQMIWXHGXVSAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  2-chloro-8-methoxy-11H-indolo[3,2-c]quinoline 、 碘甲烷 在 硝基苯 、 ammonium hydroxide 作用下， 反应 2.0h， 以73%的产率得到2-chloro-8-methoxy-5-methyl-5H-indolo[3,2-c]quinoline
  参考文献：
  名称：

  Synthesis of isocryptolepine analogues and their structure–activity relationship studies as antiplasmodial and antiproliferative agents

  摘要：

  Novel isocryptolepine analogues have been conveniently synthesized and evaluated for antimalarial and antiproliferative activities. We have found 3-fluoro-8-bromo-isocryptolepine (1n) to have the highest activities against chloroquine-resistant chloroquine-sensitive 307, and chloroquine- and mefloquine-resistant SKF58 and SRIV35 strains. Several fluorine-substituted analogues (1b, 1n, and 1q) also showed excellent selectivities while maintaining good to excellent activities against all four Plasmodium falciparum strains. Additionally, antiproliferative properties of isocryptolepine derivatives against HepG2, HuCCA-1, MOLT-3 and A549 cancer cell lines are reported for the first time in this study. 2-Chloroisocryptolepine (1c) and benzo-fused-2-chloroisocryptolepine (1i) showed significant bioactivities whereas several novel fluorinated compounds and 2-chloro-8-bromoisocryptolepine (If) displayed excellent selectivities. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.047
• 作为产物：
  描述：

  5-甲氧基-1-[(4-甲基苯基)磺酰基]-1H-吲哚 在 三氟甲磺酸 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-chloro-8-methoxy-11H-indolo[3,2-c]quinoline
  参考文献：
  名称：

  Synthesis of isocryptolepine analogues and their structure–activity relationship studies as antiplasmodial and antiproliferative agents

  摘要：

  Novel isocryptolepine analogues have been conveniently synthesized and evaluated for antimalarial and antiproliferative activities. We have found 3-fluoro-8-bromo-isocryptolepine (1n) to have the highest activities against chloroquine-resistant chloroquine-sensitive 307, and chloroquine- and mefloquine-resistant SKF58 and SRIV35 strains. Several fluorine-substituted analogues (1b, 1n, and 1q) also showed excellent selectivities while maintaining good to excellent activities against all four Plasmodium falciparum strains. Additionally, antiproliferative properties of isocryptolepine derivatives against HepG2, HuCCA-1, MOLT-3 and A549 cancer cell lines are reported for the first time in this study. 2-Chloroisocryptolepine (1c) and benzo-fused-2-chloroisocryptolepine (1i) showed significant bioactivities whereas several novel fluorinated compounds and 2-chloro-8-bromoisocryptolepine (If) displayed excellent selectivities. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.047

文献信息

• Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern—synthesis and biological activity studies of 11H-indolo[3.2-c]quinoline derivatives
  作者：L He

  DOI：10.1016/s0223-5234(02)01420-4

  日期：2003.1

  Designed as a new group of planar molecule containing the proposed 2-phenylnaphthalene-type structure, a number of 11H-indolo[3.2-c]quinoline derivatives were synthesized and evaluated biologically. Several compounds were found to possess cytotoxic activity against the growth of human promyclocytic leukemia cells (HL-60), against the small cell lung cancer (SCLC), and showed good response in the National Cancer Institute preclinical antitumor drug discovery 60-cell line panel. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.