(2-methyl-11H-indolo[3,2-c]quinolin-6-yl)hydrazine | 649749-03-1

• 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: (2-methyl-11H-indolo[3,2-c]quinolin-6-yl)hydrazine
• CAS: 649749-03-1
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: GIVIQJFXYVADPU-UHFFFAOYSA-N

物化性质

• 熔点：
  146 °C
• 沸点：
  568.4±52.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.73
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2-methyl-11H-indolo[3,2-c]quinolin-6-yl)hydrazine 在 三乙胺 作用下， 生成 3-chloro-1-[(2-methyl-11H-indolo[3,2-c]quinolin-6-yl)amino]-4-(4-nitrophenyl)azetidin-2-one
  参考文献：
  名称：

  Mulwad; Lohar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 8, p. 1937 - 1942

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苄胺 以 乙酸酐 为溶剂， 反应 54.0h， 生成 (2-methyl-11H-indolo[3,2-c]quinolin-6-yl)hydrazine
  参考文献：
  名称：

  Ruthenium- and osmium-arene complexes of 8-substituted indolo[3,2-c]quinolines: Synthesis, X-ray diffraction structures, spectroscopic properties, and antiproliferative activity

  摘要：

  Six novel ruthenium(II)- and osmium(II)-arene complexes with indoloquinoline modified ligands containing methyl and halo substituents in position 8 of the molecule backbone have been synthesised and comprehensively characterised by spectroscopic methods (H-1, C-13 NMR, UV-Vis), ESI mass spectrometry and X-ray crystallography. Binding of indoloquinolines to a metal-arene scaffold makes the products soluble enough in biological media to allow for assaying their antiproliferative activity. The complexes were tested in three human cancer cell lines, namely A549 (non-small cell lung cancer), SW480 (colon carcinoma) and CH1 (ovarian carcinoma), yielding IC50 values in the 10(-6)-10(-7) M concentration range after continuous exposure for 96 h. Compounds with halo substituents in position 8 are more effective cytotoxic agents in vitro than the previously reported species halogenated in position 2 of the indoloquinoline backbone. High antiproliferative activity of both series of substances may be due at least in part to their potential to act as DNA intercalators. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.06.004

文献信息

• Ruthenium− and Osmium−Arene Complexes of 2-Substituted Indolo[3,2-<i>c</i>]quinolines: Synthesis, Structure, Spectroscopic Properties, and Antiproliferative Activity
  作者：Lukas K. Filak、Gerhard Mühlgassner、Felix Bacher、Alexander Roller、Mathea Sophia Galanski、Michael A. Jakupec、Bernhard K. Keppler、Vladimir B. Arion

  DOI：10.1021/om101004z

  日期：2011.1.24

  The synthesis of new modified indolo[3,2-c]quinoline ligands L-1-L-8 with metal-binding sites is reported. By coordination to ruthenium- and osmium-arene moieties 16 complexes of the type [(eta(6)-p-cymene)M(L)Cl]Cl (1a,b-8a,b), where M is Ru-II or Os-II and L is L-1-L-8, have been prepared. All compounds were comprehensively characterized by elemental analysis, electrospray ionization mass spectrometry, IR, UV-vis, and NMR spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction (2a, 4a, 4b, 5a, 7a, and 7b). The complexes were tested for antiproliferative activity in vitro in three human cancer cell lines, namely, CH1 (ovarian carcinoma), SW480 (colon adenocarcinoma), and A549 (non-small-cell lung cancer), yielding IC50 values in the submicromolar or low micromolar range.