methyl 11-(4-aminobutylamino)-5-methyl-5H-indolo[2,3-b]quinoline-9-carboxylate | 1421349-36-1

• 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: methyl 11-(4-aminobutylamino)-5-methyl-5H-indolo[2,3-b]quinoline-9-carboxylate
• 英文别名: methyl 11-(4-aminobutylamino)-5-methylindolo[2,3-b]quinoline-9-carboxylate
• CAS: 1421349-36-1
• 化学式: C₂₂H₂₄N₄O₂
• 分子量: 376.458
• InChiKey: MYYBSEQXUHAKGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  吲哚-5-甲酸甲酯 在 1,4-二甲基哌嗪 、 吡啶 、 N-氯代丁二酰亚胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二苯醚 、 甲苯 为溶剂， 反应 5.0h， 生成 methyl 11-(4-aminobutylamino)-5-methyl-5H-indolo[2,3-b]quinoline-9-carboxylate
  参考文献：
  名称：

  11-氨基烷基氨基取代的5 H-吲哚并[2,3-b]喹啉的体外抗增殖活性；通过安装酯取代基改善新隐油菜素的活性

  摘要：

  摘要该研究文章描述了酯基对5-甲基-5 H-吲哚并[2,3- b ]喹啉（新隐油菜籽）衍生物的SAR研究中体外抗增殖活性的影响。从吲哚-3-羧酸酯和N开始合成C-2和/或C-9酯取代的新隐油松-带有酯基的甲基苯胺。在这些酯取代的新隐油松上，在C-11处进一步连接了多个氨基烷基氨基取代基，并通过改变C-11处的取代基以及A和/或D中酯基的位置进行了体外抗增殖测定新隐油环的环。结果表明，通过在C-9位引入酯取代基可以改善药物的抗增殖活性。其中，11-（3-氨基丙基氨基）-5-甲基-5 H-吲哚并[2,3 - b ]喹啉-9-羧酸酯（8b）是最有效的IC 50试剂。0.044μM对人白血病MV4-11细胞株的抗 还描述了药剂在癌细胞系和正常细胞系之间的选择性细胞毒性。二甲基11-（3-氨基丙基氨基）-5-甲基-5 H-吲哚并[2,3 - b ]喹啉-2,9-二羧酸盐（9a）对人结肠癌细胞系HCT

  DOI：

  10.1007/s00044-012-0443-x

文献信息

• Synthesis and antimalarial testing of neocryptolepine analogues: Addition of ester function in SAR study of 2,11-disubstituted indolo[2,3-b]quinolines
  作者：Wen-Jie Lu、Kathryn J. Wicht、Li Wang、Kento Imai、Zhen-Wu Mei、Marcel Kaiser、Ibrahim El Tantawy El Sayed、Timothy J. Egan、Tsutomu Inokuchi

  DOI：10.1016/j.ejmech.2013.03.072

  日期：2013.6

  This report describes the synthesis, and in vitro and in vivo antimalarial evaluations of certain ester-modified neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline) derivatives. The modifications were carried out by introducing ester groups at the C2 and/or C9 position on the neocryptolepine core and the terminal amino group of the 3-aminopropylamine substituents at the C11 position with a urea/thiourea unit. The antiplasmodial activities of our derivative agents against two different strains (CQS: NF54, and CQR: R1) and the cytotoxic activity against normal L6 cells were evaluated. The test results showed that the ester modified neocryptolepine derivatives have higher antiplasmodial activities against both strains and a low cytotoxic activity against normal cells. The best results were achieved by compounds 9c and 12b against the NF54 strain with the IC50/SI value as 2.27 nM/361 and 1.81 nM/321, respectively. While against R1 strain, all the tested compounds showed higher activity than the well-known antimalarial drug chloroquine. Furthermore, the compounds were tested for beta-haematin inhibition and 12 were found to be more active than chloroquine (IC50 = 18 mu M). Structure activity relationship studies exposed an interesting linear correlation between polar surface area of the molecule and beta-haematin inhibition for this series. In vivo testing of compounds 7 and 8a against NF54 strain on Plasmodium berghei female mice showed that the introduction of the ester group increased the antiplasmodial activity of the neocryptolepine core substantially. (C) 2013 Elsevier Masson SAS. All rights reserved.
• In vitro antiproliferative activity of 11-aminoalkylamino-substituted 5H-indolo[2,3-b]quinolines; improving activity of neocryptolepines by installation of ester substituent
  作者：Wen-Jie Lu、Marta Świtalska、Li Wang、Mizuki Yonezawa、Ibrahim El-Tantawy El-Sayed、Joanna Wietrzyk、Tsutomu Inokuchi

  DOI：10.1007/s00044-012-0443-x

  日期：2013.9

  antiproliferative assay was performed by varying the substituents at the C-11 and the position of the ester group in the A and/or D ring of neocryptolepines. Results indicated that the antiproliferative activities of the agents could be improved by introducing an ester substituent at the C-9 position. Among them, the methyl 11-(3-aminopropylamino)-5-methyl-5H-indolo[2,3-b]quinoline-9-carboxylate (8b) was

  摘要该研究文章描述了酯基对5-甲基-5 H-吲哚并[2,3- b ]喹啉（新隐油菜籽）衍生物的SAR研究中体外抗增殖活性的影响。从吲哚-3-羧酸酯和N开始合成C-2和/或C-9酯取代的新隐油松-带有酯基的甲基苯胺。在这些酯取代的新隐油松上，在C-11处进一步连接了多个氨基烷基氨基取代基，并通过改变C-11处的取代基以及A和/或D中酯基的位置进行了体外抗增殖测定新隐油环的环。结果表明，通过在C-9位引入酯取代基可以改善药物的抗增殖活性。其中，11-（3-氨基丙基氨基）-5-甲基-5 H-吲哚并[2,3 - b ]喹啉-9-羧酸酯（8b）是最有效的IC 50试剂。0.044μM对人白血病MV4-11细胞株的抗 还描述了药剂在癌细胞系和正常细胞系之间的选择性细胞毒性。二甲基11-（3-氨基丙基氨基）-5-甲基-5 H-吲哚并[2,3 - b ]喹啉-2,9-二羧酸盐（9a）对人结肠癌细胞系HCT