9-ethyl-N-(pyridine-2-ylmethylene)-9H-carbazole-3-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-ethyl-N-(pyridine-2-ylmethylene)-9H-carbazole-3-amine
• 英文别名: 9-ethyl-N-(pyridin-2-ylmethylene)-9H-carbazole-3-amine；N-(9-ethylcarbazol-3-yl)-1-pyridin-2-ylmethanimine
• 化学式: C₂₀H₁₇N₃
• 分子量: 299.375
• InChiKey: IUDXVRNMXLUJOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dichloro(1,5-cyclooctadiene)ruthenium(II) 、 9-ethyl-N-(pyridine-2-ylmethylene)-9H-carbazole-3-amine 以 乙醇 为溶剂， 反应 2.0h， 以67%的产率得到
  参考文献：
  名称：

  Binding interaction, conformational change, and molecular docking study of N-(pyridin-2-ylmethylene)aniline derivatives and carbazole Ru(II) complexes with human serum albumins

  摘要：

  New [RuCl2(1,5cod)(L1)] (1), [RuCl2(1,5cod)(L2)] (2), [RuCl2(1,5cod)(L3)1 (3), [RuCl2(1,5cod)(L4)] (4), [RuCl2(1,5cod)(L5)] (5) (L = (p-R-N-(pyridin-2-ylmethylene)aniline), R = H (L1), Cl (12), OCH3 (L3), CH3 (L4), L5 = (9-ethyl-N-(pyridin-2-ylmethylene)9H-carbazole-3-amine and 1,5cod = eta(4)-cyclooctadiene) complexes were synthesized and characterized by H-1 and C-13 NMR, melting point analysis, elemental analysis, HR-Mass spectrometry, FT-IR and UV-Vis spectroscopy. The single crystal X-ray structures of complexes 1, 2 and 3 revealed coordination of the ligands to the Ru(II) center in a bidentate manner via the N atoms. The geometry around the Ru(II) center is pseudooctahedral with the two Cl atoms and the pi-bonds of the cydooctadiene occupying the coordination sites. Interactions of Ru(II) complexes 1-5 with human serum albumins (HSA) were investigated using UV-Vis, synchronous emission and circular dichroism spectroscopy. The results demonstrated that the Ru(II) complexes 1-5 have significantly strong interaction with HSA proteins. Complexes 1, 3 and 5 showed moderate-to-high binding constants (K-b) 1.77 x 10(5) dm(3) mol(-1) (1), 1.07 x 10(5) dm(3) mol(-1) (3) and 1.07 x 10(5) dm(3) mol(-1) (5) respectively. Circular dichroism (CD) studies revealed decreased alpha-helix content within HSA upon interaction with complexes 1-5, suggesting a conformational change of the HSA secondary structure. Also, molecular docking studies were carried out to identify the binding models of the HSA-Ru complexes and binding energy of complexes 1-5 in HSA, which further revealed the contribution of amino acid residues of HSA in Ru(II) complex binding. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.01.017
• 作为产物：
  描述：

  吡啶-2-甲醛 、 3-氨基-9-乙基咔唑 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以93%的产率得到9-ethyl-N-(pyridine-2-ylmethylene)-9H-carbazole-3-amine
  参考文献：
  名称：

  新的半夹心Ir（III），Rh（III）和Ru（II）配合物的合成，表征，抗增殖和分子对接研究

  摘要：

  新的咔唑-N，N'配位体含有[（η 5 -C 5我5）的MC1（大号）] PF 6，（M = IR（1）和Rh（2））和[（η 6 -C 6 H ^ 6）RuCl（L）] PF 6（3）（C 5 Me 5  =五甲基环戊二烯基，L  = 9-乙基-N-（吡啶-2-基亚甲基）-9H-咔唑-3-胺）配合物通过1 H NMR，13C NMR，2D NMR，熔点分析，电子吸收，红外光谱，HR-质谱和元素分析。所述的晶体结构[（η 5 -C 5我5）的RhCl（大号）] PF 6已经通过单晶X射线衍射证实。合成的复合物的抗癌研究1 - 3清楚地表明人乳腺癌细胞（MCF-7）的强效抑制剂下在体外条件下。的抑制浓度（IC 50）的配合物的1 - 3在针对MCF-7人乳腺癌细胞系的低（5、6和8μM）浓度下进行了检测。进一步的细胞毒性，细胞周期和核研究证实，新型半夹心Ir（III），Rh（III）和Ru（

  DOI：

  10.1016/j.jinorgbio.2016.02.006

文献信息

• Synthesis, characterization, antiproliferative and molecular docking study of new half sandwich Ir(III), Rh(III) and Ru(II) complexes
  作者：Saravanan Thangavel、Manickam Paulpandi、Holger B. Friedrich、Kadarkarai Murugan、Sukesh Kalva、Adam A. Skelton

  DOI：10.1016/j.jinorgbio.2016.02.006

  日期：2016.6

  synthesized complexes 1–3 clearly showed a potent inhibitor of human breast cancer cells (MCF-7) under in vitro conditions. The inhibitory concentrations (IC50) of the complexes 1–3 were determined at low (5, 6 and 8 μM) concentration against the MCF-7 human breast cancer cell line. Further cytotoxic, cell cycle and nuclear studies confirmed that the novel half sandwich Ir(III), Rh(III) and Ru(II)

  新的咔唑-N，N'配位体含有[（η 5 -C 5我5）的MC1（大号）] PF 6，（M = IR（1）和Rh（2））和[（η 6 -C 6 H ^ 6）RuCl（L）] PF 6（3）（C 5 Me 5  =五甲基环戊二烯基，L  = 9-乙基-N-（吡啶-2-基亚甲基）-9H-咔唑-3-胺）配合物通过1 H NMR，13C NMR，2D NMR，熔点分析，电子吸收，红外光谱，HR-质谱和元素分析。所述的晶体结构[（η 5 -C 5我5）的RhCl（大号）] PF 6已经通过单晶X射线衍射证实。合成的复合物的抗癌研究1 - 3清楚地表明人乳腺癌细胞（MCF-7）的强效抑制剂下在体外条件下。的抑制浓度（IC 50）的配合物的1 - 3在针对MCF-7人乳腺癌细胞系的低（5、6和8μM）浓度下进行了检测。进一步的细胞毒性，细胞周期和核研究证实，新型半夹心Ir（III），Rh（III）和Ru（
• New Ru(II) half sandwich complexes bearing the N,N′ bidentate 9-ethyl-N-(pyridin-2-ylmethylene)9H-carbazole-3-amine ligand: Effects of halogen (Cl−, Br− and I−) leaving groups versus in vitro activity on HepG2 cancer cells, cell cycle, fluorescence study, cellular accumulation and DFT study
  作者：Saravanan Thangavel、Manickam Paulpandi、Holger B. Friedrich、Kalva Sukesh、Adam A. Skelton

  DOI：10.1016/j.poly.2018.05.060

  日期：2018.9

  shown that the new Ru(II) half sandwich complexes 1–3 were effective against HepG2 cancer cell proliferation. Density functional theory (DFT) was used to calculate the relevant molecular orbital energy levels, binding energies, bond angles and bond lengths of the synthesised Ru(II) complexes. The DFT study of the complexes 1–3 further supported the biological activity of the complexes and showed good

  摘要三种新的钌（II）配合物[（η6-p-cymene）RuX（L）] PF6（X = Cl（1），Br（2）和I（3））与9-乙基-N-（吡啶-已经制备了2-基亚甲基）9H-咔唑-3-胺（L），并通过元素分析和不同的光谱技术（NMR研究，IR和HR-质谱分析）对其进行了表征。通过单晶XRD确定[（η6-对-cymene）RuI（L）] PF6（3）配合物的分子结构。Ru（II）中心周围的几何结构是经典的“钢琴凳”，其具有碘，N，N'配体以双齿方式键合，对苯丙氨酸的π键占据了配位点。对HepG2人肝癌细胞上的1-3复合物的体外研究显示，其抑菌浓度（IC50）值极佳，介于22和30μM之间。卤素离去基团Cl-，配合物1-3中的Br-和I-表现出显著作用。有趣的是，与其他两种复合物相比，复合物3显示出22μM的显着生长抑制IC50值。此外，细胞周期，细胞毒性，核研究和细胞蓄积表明，新的Ru（I
• Binding interaction, conformational change, and molecular docking study of N-(pyridin-2-ylmethylene)aniline derivatives and carbazole Ru(II) complexes with human serum albumins
  作者：Saravanan Thangavel、Ramar Rajamanikandan、Holger B. Friedrich、Malaichamy Ilanchelian、Bernard Omondi

  DOI：10.1016/j.poly.2016.01.017

  日期：2016.3

  New [RuCl2(1,5cod)(L1)] (1), [RuCl2(1,5cod)(L2)] (2), [RuCl2(1,5cod)(L3)1 (3), [RuCl2(1,5cod)(L4)] (4), [RuCl2(1,5cod)(L5)] (5) (L = (p-R-N-(pyridin-2-ylmethylene)aniline), R = H (L1), Cl (12), OCH3 (L3), CH3 (L4), L5 = (9-ethyl-N-(pyridin-2-ylmethylene)9H-carbazole-3-amine and 1,5cod = eta(4)-cyclooctadiene) complexes were synthesized and characterized by H-1 and C-13 NMR, melting point analysis, elemental analysis, HR-Mass spectrometry, FT-IR and UV-Vis spectroscopy. The single crystal X-ray structures of complexes 1, 2 and 3 revealed coordination of the ligands to the Ru(II) center in a bidentate manner via the N atoms. The geometry around the Ru(II) center is pseudooctahedral with the two Cl atoms and the pi-bonds of the cydooctadiene occupying the coordination sites. Interactions of Ru(II) complexes 1-5 with human serum albumins (HSA) were investigated using UV-Vis, synchronous emission and circular dichroism spectroscopy. The results demonstrated that the Ru(II) complexes 1-5 have significantly strong interaction with HSA proteins. Complexes 1, 3 and 5 showed moderate-to-high binding constants (K-b) 1.77 x 10(5) dm(3) mol(-1) (1), 1.07 x 10(5) dm(3) mol(-1) (3) and 1.07 x 10(5) dm(3) mol(-1) (5) respectively. Circular dichroism (CD) studies revealed decreased alpha-helix content within HSA upon interaction with complexes 1-5, suggesting a conformational change of the HSA secondary structure. Also, molecular docking studies were carried out to identify the binding models of the HSA-Ru complexes and binding energy of complexes 1-5 in HSA, which further revealed the contribution of amino acid residues of HSA in Ru(II) complex binding. (C) 2016 Elsevier Ltd. All rights reserved.