N-<2-(dimethylamino)ethyl>-11H-indeno<1,2-b>quinolin-10-amine | 137434-38-9

• 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-<2-(dimethylamino)ethyl>-11H-indeno<1,2-b>quinolin-10-amine
• 英文别名: 11H-indeno[1,2-b]quinolin-10-yl-(N,N-dimethylethylenediamine)；N¹-(11H-indeno[1,2-b]quinolin-10-yl)-N²,N²-dimethylethane-1,2-diamine；10-[2-(Dimethylamino)ethylamino]-6H-indeno[2,1-b]quinoline；N-(11H-indeno[1,2-b]quinolin-10-yl)-N',N'-dimethylethane-1,2-diamine
• CAS: 137434-38-9
• 化学式: C₂₀H₂₁N₃
• 分子量: 303.407
• InChiKey: DMRFORMHEBXQFL-UHFFFAOYSA-N

物化性质

• 沸点：
  505.8±50.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5H-indeno[1,2-b]quinolin-10(11H)-one 在 三氯氧磷 作用下， 以 乙二醇 为溶剂， 生成 N-<2-(dimethylamino)ethyl>-11H-indeno<1,2-b>quinolin-10-amine
  参考文献：
  名称：

  Cryptolepine and aromathecin based mimics as potent G-quadruplex-binding, DNA-cleavage and anticancer agents: Design, synthesis and DNA targeting-induced apoptosis

  摘要：

  Thirty Cryptolepine and Aromathecin based mimics were designed and synthesized. Their cytotoxicity was evaluated in four human cancer cell lines (HepG-2, T24, NCI-H460 and MGC-803) and one normal human cell line (HL-7702). Most compounds exhibited potent anticancer activity with IC50 values from 0.31 to 11.97 mu M. 8-Fluoro-10-(N-3-dimethylaminopropyl)amino-11H-indeno[1,2-b]quinoline (5b) was identified as the most promising candidate in view of its anticancer activity. Molecular mechanism studies suggested that 5b not only could strongly bind to G-quadruplex, but intercalate into supercoil DNA and resulted in significant DNA double-strand break as well. Furthermore, 5b caused cell cycle arrest at S/G2 phase and induced apoptosis. After treatment with 5b, pro-apoptotic proteins Bak, Bax and Bim were up-regulated, anti-apoptotic proteins Bcl-2 and Bcl-xL were down-regulated, and the effector caspase-3/9 was activated to initiate apoptosis. The anticancer activity of 5b was finally validated in a MGC-803 xenograft tumor model with tumor growth inhibition (TGI) up to 53.2%, while displaying no obvious toxicity. Taken together, these results suggest that 5b may be a potential candidate of cytotoxic antineoplastic drugs for cancer therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.072

文献信息

• 一种新的[1,2,b]茚并喹啉类衍生物及其制备 方法和在抗肿瘤药物中的应用
  申请人：广西师范大学

  公开号：CN105622508B

  公开（公告）日：2018-08-21

  本发明公开了一种新的茚并[1,2,b]喹啉类衍生物及其制备方法，衍生物的结构通式为：这种衍生物具有良好的体内、外抗肿瘤活性，可以制备成抗肿瘤的药物。
• Further studies on the cyclization of aromatic azomethines ortho-substituted with a trifluoromethyl group: synthesis of 2,4-di- or 2,3,4-trisubstituted quinolines
  作者：Lucjan Strekowski、Steven E. Patterson、Lubomir Janda、Roman L. Wydra、Donald B. Harden、Malgorzata Lipowska、Marek T. Cegla

  DOI：10.1021/jo00027a037

  日期：1992.1

  The scope and limitations of the novel synthetic route to quinolines (Strekowski et al. J. Org. Chem. 1990, 55, 4777) have been studied. A direct condensation of 2-(trifluoromethyl)aniline (1) with methyl aryl ketones, methyl heteroaryl ketones, ethyl aryl ketones, methyl vinyl ketones, 1-indanone, 1-tetralone, camphor, and cyclohexanone provides an easy access to the corresponding ketimines. An indirect one-pot preparation of dialkyl ketimines and C-alkyl-substituted amidines derived from 1, but inaccessible by the direct condensation method, is also presented. All these ketimines and amidines are cyclized in the presence of alkylamide, dialkylamide, or alkoxide bases to give a quinoline containing the base function at C-4. Analysis of byproducts of the base-mediated reactions provides strong support for the originally proposed mechanism of the quinoline formation.
• Cryptolepine and aromathecin based mimics as potent G-quadruplex-binding, DNA-cleavage and anticancer agents: Design, synthesis and DNA targeting-induced apoptosis
  作者：Jing-Mei Yuan、Kai Wei、Guo-Hai Zhang、Nan-Ying Chen、Xin-Wei Wei、Cheng-Xue Pan、Dong-Liang Mo、Gui-Fa Su

  DOI：10.1016/j.ejmech.2019.02.072

  日期：2019.5

  Thirty Cryptolepine and Aromathecin based mimics were designed and synthesized. Their cytotoxicity was evaluated in four human cancer cell lines (HepG-2, T24, NCI-H460 and MGC-803) and one normal human cell line (HL-7702). Most compounds exhibited potent anticancer activity with IC50 values from 0.31 to 11.97 mu M. 8-Fluoro-10-(N-3-dimethylaminopropyl)amino-11H-indeno[1,2-b]quinoline (5b) was identified as the most promising candidate in view of its anticancer activity. Molecular mechanism studies suggested that 5b not only could strongly bind to G-quadruplex, but intercalate into supercoil DNA and resulted in significant DNA double-strand break as well. Furthermore, 5b caused cell cycle arrest at S/G2 phase and induced apoptosis. After treatment with 5b, pro-apoptotic proteins Bak, Bax and Bim were up-regulated, anti-apoptotic proteins Bcl-2 and Bcl-xL were down-regulated, and the effector caspase-3/9 was activated to initiate apoptosis. The anticancer activity of 5b was finally validated in a MGC-803 xenograft tumor model with tumor growth inhibition (TGI) up to 53.2%, while displaying no obvious toxicity. Taken together, these results suggest that 5b may be a potential candidate of cytotoxic antineoplastic drugs for cancer therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.