6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo[3,2-d][1]benzazepine | 1202937-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo[3,2-d][1]benzazepine
• 英文别名: N'-(7,12-dihydroindolo[3,2-d][1]benzazepin-6-yl)-N,N-dimethylethane-1,2-diamine；N'-(7,12-dihydroindolo-[3,2-d][1]benzazepin-6-yl)-N,N-dimethylethane-1,2-diamine；2-(7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-ylideneamino)-N,N-dimethylethanamine
• CAS: 1202937-89-0
• 化学式: C₂₀H₂₂N₄
• 分子量: 318.421
• InChiKey: DBVIDQFBVQWYDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  43.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo[3,2-d][1]benzazepine 以 甲醇 为溶剂， 以69%的产率得到6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo[3,2-d][1]benzazepino-dichlorido-copper(II)
  参考文献：
  名称：

  Highly Cytotoxic Copper(II) Complexes with Modified Paullone Ligands

  摘要：

  The reaction of copper(II) chloride or copper(II) acetate with 6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo-[3,2-d][1]benzazepine (HL1), 9-bromo-6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo[3,2-d][1]-benzazepine (HL2), N-(9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-yliden-N'-(1-pyridin-2-yl-methylidene)azine (HL3), or N-(9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-yliden-N'-(1-pyridin-2-yl-ethylidene)azine (HL4) in methanol affords the novel copper(I-I) complexes [Cu(HL1)Cl-2] (1). [Cu(HL2)Cl-2] (2). [Cu(HL3)Cl-2] (3), [Cu(HL4)Cl-2] (4), and [Cu(L-4)(CH3COO)(CH3OH)] (5). The new ligands (HL2 and HL3) and the complexes 1-5 were characterized by H-1 and C-13 NMR, IR and electronic absorption spectroscopy, ESI mass spectrometry, and X-ray crystallography. Two ligands, HL1 and HL2, and complexes 1-4 were tested for cytotoxicity in three human cancer cell lines, namely, CH1 (ovarian carcinoma), A549 (non-small cell lung cancer), and SW480 (colon carcinoma). Additionally, complexes 1, 2, and 4 were assayed in an isogenic pair of ovarian cancer cell lines, one being sensitive to cisplatin (A2780) and the other having acquired cisplatin resistance (A2780cisR). All of the compounds evaluated are cytotoxic, with complexes 3 and 4 exhibiting IC50 values in the nanomolar range.

  DOI：

  10.1021/ic902042a
• 作为产物：
  描述：

  N,N-二甲基乙二胺 、 7,12-Dihydroindolo<3,2-d><1>benzazepin-6(5H)-thion 以 四氢呋喃 为溶剂， 反应 26.0h， 以72%的产率得到6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo[3,2-d][1]benzazepine
  参考文献：
  名称：

  有机金属吲哚 [3,2-c] 喹啉与吲哚 [3,2-d] 苯并氮杂：合成、结构和光谱表征以及生物学功效。

  摘要：

  这些化合物已通过元素分析、电喷雾电离质谱、光谱（IR、UV-vis 和 NMR）和 X 射线晶体学（L ( 1 ).HCl, 4.H(2)O, 5,和 9.2.5H(2)O)。已经建立了关于人类癌细胞中的细胞毒性和细胞周期效应以及细胞周期蛋白依赖性激酶 (cdk) 抑制和无细胞环境中的 DNA 嵌入的构效关系。不含金属的吲哚 [3,2-c] 喹啉在体外抑制癌细胞生长，IC(50) 值在高纳摩尔范围内，而相关的吲哚 [3,2-d] 苯并氮杂的 IC(50) 值在低微摩尔范围。在无细胞实验中，这些类别的化合物抑制 cdk2/cyclin E 的活性，

  DOI：

  10.1007/s00775-010-0653-y

文献信息

• Organometallic indolo[3,2-c]quinolines versus indolo[3,2-d]benzazepines: synthesis, structural and spectroscopic characterization, and biological efficacy
  作者：Lukas K. Filak、Gerhard Mühlgassner、Michael A. Jakupec、Petra Heffeter、Walter Berger、Vladimir B. Arion、Bernhard K. Keppler

  DOI：10.1007/s00775-010-0653-y

  日期：2010.8

  The synthesis of ruthenium(II) and osmium(II) arene complexes with the closely related indolo[3,2-c]quinolines N-(11H-indolo[3,2-c]quinolin-6-yl)-ethane-1,2-diamine (L ( 1 )) and N'-(11H-indolo[3,2-c]quinolin-6-yl)-N,N-dimethylethane-1,2-diamine (L ( 2 )) and indolo[3,2-d]benzazepines N-(7,12-dihydroindolo-[3,2-d][1]benzazepin-6-yl)-ethane-1,2-diamine (L ( 3 )) and N'-(7,12-dihydroindolo-[3,2-d][1]benzazepin-6-yl)-N

  这些化合物已通过元素分析、电喷雾电离质谱、光谱（IR、UV-vis 和 NMR）和 X 射线晶体学（L ( 1 ).HCl, 4.H(2)O, 5,和 9.2.5H(2)O)。已经建立了关于人类癌细胞中的细胞毒性和细胞周期效应以及细胞周期蛋白依赖性激酶 (cdk) 抑制和无细胞环境中的 DNA 嵌入的构效关系。不含金属的吲哚 [3,2-c] 喹啉在体外抑制癌细胞生长，IC(50) 值在高纳摩尔范围内，而相关的吲哚 [3,2-d] 苯并氮杂的 IC(50) 值在低微摩尔范围。在无细胞实验中，这些类别的化合物抑制 cdk2/cyclin E 的活性，
• Highly Cytotoxic Copper(II) Complexes with Modified Paullone Ligands
  作者：Michael F. Primik、Gerhard Mühlgassner、Michael A. Jakupec、Olivier Zava、Paul J. Dyson、Vladimir B. Arion、Bernhard K. Keppler

  DOI：10.1021/ic902042a

  日期：2010.1.4

  The reaction of copper(II) chloride or copper(II) acetate with 6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo-[3,2-d][1]benzazepine (HL1), 9-bromo-6-N-(2-N',N'-dimethylaminoethylamino)-7,12-dihydroindolo[3,2-d][1]-benzazepine (HL2), N-(9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-yliden-N'-(1-pyridin-2-yl-methylidene)azine (HL3), or N-(9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-yliden-N'-(1-pyridin-2-yl-ethylidene)azine (HL4) in methanol affords the novel copper(I-I) complexes [Cu(HL1)Cl-2] (1). [Cu(HL2)Cl-2] (2). [Cu(HL3)Cl-2] (3), [Cu(HL4)Cl-2] (4), and [Cu(L-4)(CH3COO)(CH3OH)] (5). The new ligands (HL2 and HL3) and the complexes 1-5 were characterized by H-1 and C-13 NMR, IR and electronic absorption spectroscopy, ESI mass spectrometry, and X-ray crystallography. Two ligands, HL1 and HL2, and complexes 1-4 were tested for cytotoxicity in three human cancer cell lines, namely, CH1 (ovarian carcinoma), A549 (non-small cell lung cancer), and SW480 (colon carcinoma). Additionally, complexes 1, 2, and 4 were assayed in an isogenic pair of ovarian cancer cell lines, one being sensitive to cisplatin (A2780) and the other having acquired cisplatin resistance (A2780cisR). All of the compounds evaluated are cytotoxic, with complexes 3 and 4 exhibiting IC50 values in the nanomolar range.