N¹,N¹-diethyl-N⁴-(11-methyl-11H-indolo[3,2-c]quinolin-6-yl)pentane-1,4-diamine | 1608153-30-5

• 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: N¹,N¹-diethyl-N⁴-(11-methyl-11H-indolo[3,2-c]quinolin-6-yl)pentane-1,4-diamine
• 英文别名: N¹-(2-bromo-11-methyl-11H-indolo[3,2-c]quinolin-6-yl)propane-1,3-diamine；1-N,1-N-diethyl-4-N-(11-methylindolo[3,2-c]quinolin-6-yl)pentane-1,4-diamine
• CAS: 1608153-30-5
• 化学式: C₂₅H₃₂N₄
• 分子量: 388.556
• InChiKey: FNWWRLHCNWEJSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,11-二氢-6H-吲哚并[3,2-c]喹啉-6-酮 在 sodium hydride 、 三氯氧磷 作用下， 以 mineral oil 为溶剂， 反应 12.0h， 生成 N¹,N¹-diethyl-N⁴-(11-methyl-11H-indolo[3,2-c]quinolin-6-yl)pentane-1,4-diamine
  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 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.