6-(2-dimethylaminoethyl)-11-methyl-6H-indolo[2,3-b]quinolin-9-yl-amine | 1402935-89-0

• 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: 6-(2-dimethylaminoethyl)-11-methyl-6H-indolo[2,3-b]quinolin-9-yl-amine
• 英文别名: 6-[2-(Dimethylamino)ethyl]-11-methylindolo[2,3-b]quinolin-9-amine；6-[2-(dimethylamino)ethyl]-11-methylindolo[2,3-b]quinolin-9-amine
• CAS: 1402935-89-0
• 化学式: C₂₀H₂₂N₄
• 分子量: 318.421
• InChiKey: XQODMZCEGUYXDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-dimethylaminoethyl)-11-methyl-6H-indolo[2,3-b]quinolin-9-yl-amine 在 吡啶 、 硫酸 、 四丁基溴化铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 N-[6-(2-dimethylaminoethyl)-11-methyl-6H-indolo[2,3-b]quinol-9-yl]-N-(2-dimethylaminoethyl)-p-toluenesulfonamide
  参考文献：
  名称：

  New derivatives of 11-methyl-6-[2-(dimethylamino)ethyl]-6H-indolo[2,3-b]quinoline as cytotoxic DNA topoisomerase II inhibitors

  摘要：

  Novelindolo[2,3-b]quinoline derivatives substituted at N-6 and C-2 or C-9 positions with (dimethylamino) ethyl chains linked to heteroaromatic core by ether, amide or amine bonds, were manufactured and evaluated in vitro for their cytotoxic activity against several cell lines of different origin including multidrug resistant sublines and tested for their ability to influence the cell cycle and inhibit topoisomerase II activity. It was found, that all compounds show cytotoxic activity against cell lines tested, including multidrug resistant LoVo/DX, MES-SA/DX5 and HL-60 sublines. The tested compounds induce the G(2)M phase cell cycle arrest in Jurkat cells, and inhibit topoisomerase II activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.032
• 作为产物：
  描述：

  11-methyl-9-nitro-6H-indolo[2,3-b]quinoline 在 盐酸 、 四丁基溴化铵 、 tin(ll) chloride 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 6.5h， 生成 6-(2-dimethylaminoethyl)-11-methyl-6H-indolo[2,3-b]quinolin-9-yl-amine
  参考文献：
  名称：

  New derivatives of 11-methyl-6-[2-(dimethylamino)ethyl]-6H-indolo[2,3-b]quinoline as cytotoxic DNA topoisomerase II inhibitors

  摘要：

  Novelindolo[2,3-b]quinoline derivatives substituted at N-6 and C-2 or C-9 positions with (dimethylamino) ethyl chains linked to heteroaromatic core by ether, amide or amine bonds, were manufactured and evaluated in vitro for their cytotoxic activity against several cell lines of different origin including multidrug resistant sublines and tested for their ability to influence the cell cycle and inhibit topoisomerase II activity. It was found, that all compounds show cytotoxic activity against cell lines tested, including multidrug resistant LoVo/DX, MES-SA/DX5 and HL-60 sublines. The tested compounds induce the G(2)M phase cell cycle arrest in Jurkat cells, and inhibit topoisomerase II activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.032

文献信息

• The synthesis of indolo[2,3-b]quinoline derivatives with a guanidine group: Highly selective cytotoxic agents
  作者：Katarzyna Sidoryk、Marta Świtalska、Anna Jaromin、Piotr Cmoch、Iwona Bujak、Monika Kaczmarska、Joanna Wietrzyk、Eddie G. Dominguez、Robert Żarnowski、David R. Andes、Krzysztof Bańkowski、Marcin Cybulski、Łukasz Kaczmarek

  DOI：10.1016/j.ejmech.2015.10.022

  日期：2015.11

  The synthesis of indolo[2,3-b]quinoline derivatives containing guanidine, amino acid or guanylamino acid substituents as well as their in vitro evaluation for the cytotoxic and antifungal activity are reported. The influence of the guanidine group on the selective cytotoxic and hemolytic properties of indolo[2,3-b]quinoline was investigated. Most of the compounds displayed a high cytotoxic activity

  报道了含有胍，氨基酸或胍基氨基酸取代基的吲哚并[2,3-b]喹啉衍生物的合成及其细胞毒性和抗真菌活性的体外评价。研究了胍基对吲哚[2,3-b]喹啉的选择性细胞毒性和溶血特性的影响。大多数化合物在体外显示出高的细胞毒性活性，而两种最有希望的化合物（3和12）在正常细胞系和癌细胞系之间显示出高选择性。化合物3对正常成纤维细胞的细胞毒性活性比对A549和MCF-7癌细胞系的细胞毒性活性低约600倍。当使用DNA-甲基绿色测定法进行测试时，新型实体可充当DNA嵌入剂，但与它们的未取代类似物相比，其溶血活性为零或较低。
• An efficient synthesis of indolo[2,3-b]quinoline guanidine derivatives with their in vitro and in vivo study
  作者：Katarzyna Sidoryk、Marta Świtalska、Piotr Rózga、Joanna Wietrzyk、Iwona Bujak、Bartłomiej Żerek、Łukasz Kaczmarek、Marcin Cybulski

  DOI：10.1007/s00044-017-2028-1

  日期：2017.12

  verifying the efficacy of common guanylation reagents in order to obtain the guanidine derivatives of indolo[2,3-b]quinoline has been performed. As a result, a high-yield procedure using N,N′-di-Boc-N′′-triflylguanidine was applied to synthesize the guanidine derivative of indolo[2,3-b]quinoline 1 in a gram scale for specific in vitro and in vivo biological research. Extensive studies on the antiproliferative

  为了验证吲哚并[2,3-b]喹啉的胍衍生物，通过验证常用的胍化试剂的功效来优化胍基化工艺。其结果是，使用高产量过程Ñ，Ñ ' -二-制备Boc- Ñ ''-triflylguanidine施加到合成吲哚并[2,3-B]的胍衍生物的喹啉1在一克规模为特定的体外和体内生物学研究。关于八种人类肿瘤细胞系的抗增殖活性的广泛研究已经完成。化合物1显示出针对A549肺腺癌和MCF7乳腺癌细胞系的最高活性。因此，1在小鼠模型中评估了其对4T1乳腺癌和KLN205鼠肺癌的体内抗癌活性。在KLN205模型中观察到抗癌作用，在20 mg / kg剂量下具有37％的肿瘤生长抑制作用。1的抗癌活性与环磷酰胺在100 mg / kg的剂量下可抑制鼠肺肿瘤生长的27-43％相当。1次入院后的生化研究，包括测量血液参数如丙氨酸转氨酶，天冬氨酸转氨酶，乳酸脱氢酶，尿素和肌酐。
• New derivatives of 11-methyl-6-[2-(dimethylamino)ethyl]-6H-indolo[2,3-b]quinoline as cytotoxic DNA topoisomerase II inhibitors
  作者：Wojciech Luniewski、Joanna Wietrzyk、Joanna Godlewska、Marta Switalska、Malgorzata Piskozub、Wanda Peczynska-Czoch、Lukasz Kaczmarek

  DOI：10.1016/j.bmcl.2012.08.032

  日期：2012.10

  Novelindolo[2,3-b]quinoline derivatives substituted at N-6 and C-2 or C-9 positions with (dimethylamino) ethyl chains linked to heteroaromatic core by ether, amide or amine bonds, were manufactured and evaluated in vitro for their cytotoxic activity against several cell lines of different origin including multidrug resistant sublines and tested for their ability to influence the cell cycle and inhibit topoisomerase II activity. It was found, that all compounds show cytotoxic activity against cell lines tested, including multidrug resistant LoVo/DX, MES-SA/DX5 and HL-60 sublines. The tested compounds induce the G(2)M phase cell cycle arrest in Jurkat cells, and inhibit topoisomerase II activity. (C) 2012 Elsevier Ltd. All rights reserved.