N-phenyl-11H-indolo[3,2-c]quinolin-6-amine | 1224507-40-7

• 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: N-phenyl-11H-indolo[3,2-c]quinolin-6-amine
• 英文别名: (11H-indolo[3,2-c]quinolin-6-yl)phenylamine；6-(Phenylamino)-11h-indolo[3,2-c]quinoline
• CAS: 1224507-40-7
• 化学式: C₂₁H₁₅N₃
• 分子量: 309.37
• InChiKey: WKMWKSBFTLWIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  靛红 在 溶剂黄146 、 三氯氧磷 作用下， 反应 8.0h， 生成 N-phenyl-11H-indolo[3,2-c]quinolin-6-amine
  参考文献：
  名称：

  Synthesis and in vitro cytotoxic effect of 6-amino-substituted 11H- and 11Me-indolo[3,2-c]quinolines

  摘要：

  A series of 6-amino-11H- indolo[3,2-c]quinoline derivatives with various substituents on the quinoline ring were synthesized. A methyl group introduced to N-11 of the intermediate 4 to elaborate novel analog 7. The cytotoxic effect of these 6-amino-substituted 11H- and 11-methyl-indolo[3,2-c]quinoline derivatives in vitro were tested against MV4-11 (human leukemia), A549 (non-small cell lung cancer) and HCT116 (colon cancer) and BALB/3T3 (normal murine fibroblasts). All the N-11 methylated compounds significantly increased the cytotoxicity. Compound 7p was most active with the IC50 value of 0.052 mu M against the MV4-11 cell line, and also exhibited a selective activity against A549, HCT116 and BALB/3T3 cell line, with the respective IC50 values of 0.112, 0.007 and 0.083 mu M, which were higher or comparable to those of the anticancer drug doxorubicin HCl. The binding constants of 5g and 7h to salmon fish sperm DNA were also evaluated using UV-vis absorption spectroscopy, indicating intercalation binding with constants of 1.05 x 10(6) L/mol and 4.84 x 10(6) L/mol. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.038

文献信息

• Synthesis and antiproliferative evaluation of certain indolo[3,2-c]quinoline derivatives
  作者：Chih-Ming Lu、Yeh-Long Chen、Hui-Ling Chen、Chyi-An Chen、Pei-Jung Lu、Chia-Ning Yang、Cherng-Chyi Tzeng

  DOI：10.1016/j.bmc.2010.01.033

  日期：2010.3

  The present report describes the synthesis and antiproliferative evaluation of certain indolo[3,2-c]quinoline derivatives. For the C6 anilino-substituted derivatives, (11H-indolo[3,2-c]quinolin-6-yl)phenylamine (6a) was inactive. Structural optimization of 6a by the introduction of a hydroxyl group at the anilino-moiety resulted in the enhancement of antiproliferative activity in which the activity

  本报告描述了某些吲哚并[3,2- c ]喹啉衍生物的合成和抗增殖评价。对于C 6苯胺基取代的衍生物，（11 H-吲哚并[3，2 - c ]喹啉-6-基）苯胺（6a）是不活泼的。通过在苯胺基部分引入羟基来优化6a的结构导致抗增殖活性增强，其中活性按对-OH，7a  > 间位-OH，8a  > 邻位-OH，9a的顺序降低。对于C 6烷基氨基取代的衍生物11a，12a，13a，14a和15a对所有测试的癌细胞和底特律551皮肤正常成纤维细胞均表现出相当的抗增殖活性。HeLa，A549和SKHep这三种癌细胞非常敏感，IC 50小于2.17μM，而PC-3对这组吲哚[3,2- c ]喹啉具有相对抗性。对于-2-苯乙氨基衍生物，化合物20A是对HeLa细胞的具有IC的生长活性50 0.52μM的，但是对活塞551的与IC生长不太有效50为19.32μM。对于双吲哚并[3,2- Ç〕喹啉，Ñ，ñ -双-
• Synthesis and in vitro cytotoxic effect of 6-amino-substituted 11H- and 11Me-indolo[3,2-c]quinolines
  作者：Ning Wang、Marta Świtalska、Ming-Yu Wu、Kento Imai、Tran Anh Ngoc、Cui-Qing Pang、Li Wang、Joanna Wietrzyk、Tsutomu Inokuchi

  DOI：10.1016/j.ejmech.2014.03.038

  日期：2014.5

  A series of 6-amino-11H- indolo[3,2-c]quinoline derivatives with various substituents on the quinoline ring were synthesized. A methyl group introduced to N-11 of the intermediate 4 to elaborate novel analog 7. The cytotoxic effect of these 6-amino-substituted 11H- and 11-methyl-indolo[3,2-c]quinoline derivatives in vitro were tested against MV4-11 (human leukemia), A549 (non-small cell lung cancer) and HCT116 (colon cancer) and BALB/3T3 (normal murine fibroblasts). All the N-11 methylated compounds significantly increased the cytotoxicity. Compound 7p was most active with the IC50 value of 0.052 mu M against the MV4-11 cell line, and also exhibited a selective activity against A549, HCT116 and BALB/3T3 cell line, with the respective IC50 values of 0.112, 0.007 and 0.083 mu M, which were higher or comparable to those of the anticancer drug doxorubicin HCl. The binding constants of 5g and 7h to salmon fish sperm DNA were also evaluated using UV-vis absorption spectroscopy, indicating intercalation binding with constants of 1.05 x 10(6) L/mol and 4.84 x 10(6) L/mol. (C) 2014 Elsevier Masson SAS. All rights reserved.