1-(anthracen-9-yl)-N-(pyridin-3-ylmethyl)methanamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(anthracen-9-yl)-N-(pyridin-3-ylmethyl)methanamine
• 英文别名: (E)-[(Anthracen-9-YL)methylidene][(pyridin-3-YL)methyl]amine；1-anthracen-9-yl-N-(pyridin-3-ylmethyl)methanimine
• 化学式: C₂₁H₁₆N₂
• mdl: MFCD03447428
• 分子量: 296.371
• InChiKey: HMFCINRWOICMSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1-(anthracen-9-yl)-N-(pyridin-3-ylmethyl)methanamine 以 氯仿 为溶剂， 反应 5.0h， 以76%的产率得到Ru(p-cymene)(L₁)Cl₂
  参考文献：
  名称：

  Inorganic mesoporous silicas as vehicles of two novel anthracene-based ruthenium metalloarenes

  摘要：

  Two novel anthracene-based half-sandwich organometallic Ru(II) compounds, namely, [Ru(p-cymene)(L-1)Cl-2] (1) and [Ru(p-cymene)(L-2)Cl-2] (2) (L-1 = 1-(anthracen-9-yI)-N-(pyridin-3-ylmethyl)methanamine; L-2 = 1-(anthracen-9-y1)-N-(pyridin-4-ylmethyl)methanamine) have been synthesized and characterized. We demonstrate that the fluorescence properties of these complexes are highly affected by the linking position of the anthracene unit, as only 2 shows fluorescence emission in the blue region. Regarding their biological activity, both ruthenium metallodrugs show interaction with different biological targets such as S-donor amino acids (cysteine) and proteases (cysteine cathepsin B). Moreover, 1 and 2 show in vitro cytotoxicity against HL-60 cancer cell line (IC50 = 84.5 and 87.0 mu M for 1 and 2, respectively), with cell death occurring via apoptosis. Further studies have shown that diffusion into cells is the main mechanism of metallodrug uptake. Finally, as a proof of concept, these ruthenium complexes have been successfully encapsulated into MCM-41 and SBA-15 mesoporous silicas using two different incorporation strategies (impregnation and grinding). (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2016.11.004
• 作为产物：
  描述：

  3-氨甲基吡啶 、 9-蒽甲醛 以 乙醇 为溶剂， 反应 2.0h， 以86%的产率得到1-(anthracen-9-yl)-N-(pyridin-3-ylmethyl)methanamine
  参考文献：
  名称：

  Inorganic mesoporous silicas as vehicles of two novel anthracene-based ruthenium metalloarenes

  摘要：

  Two novel anthracene-based half-sandwich organometallic Ru(II) compounds, namely, [Ru(p-cymene)(L-1)Cl-2] (1) and [Ru(p-cymene)(L-2)Cl-2] (2) (L-1 = 1-(anthracen-9-yI)-N-(pyridin-3-ylmethyl)methanamine; L-2 = 1-(anthracen-9-y1)-N-(pyridin-4-ylmethyl)methanamine) have been synthesized and characterized. We demonstrate that the fluorescence properties of these complexes are highly affected by the linking position of the anthracene unit, as only 2 shows fluorescence emission in the blue region. Regarding their biological activity, both ruthenium metallodrugs show interaction with different biological targets such as S-donor amino acids (cysteine) and proteases (cysteine cathepsin B). Moreover, 1 and 2 show in vitro cytotoxicity against HL-60 cancer cell line (IC50 = 84.5 and 87.0 mu M for 1 and 2, respectively), with cell death occurring via apoptosis. Further studies have shown that diffusion into cells is the main mechanism of metallodrug uptake. Finally, as a proof of concept, these ruthenium complexes have been successfully encapsulated into MCM-41 and SBA-15 mesoporous silicas using two different incorporation strategies (impregnation and grinding). (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2016.11.004

文献信息

• Inorganic mesoporous silicas as vehicles of two novel anthracene-based ruthenium metalloarenes
  作者：Sara Rojas、Francisco J. Carmona、Elisa Barea、Carmen R. Maldonado

  DOI：10.1016/j.jinorgbio.2016.11.004

  日期：2017.1

  Two novel anthracene-based half-sandwich organometallic Ru(II) compounds, namely, [Ru(p-cymene)(L-1)Cl-2] (1) and [Ru(p-cymene)(L-2)Cl-2] (2) (L-1 = 1-(anthracen-9-yI)-N-(pyridin-3-ylmethyl)methanamine; L-2 = 1-(anthracen-9-y1)-N-(pyridin-4-ylmethyl)methanamine) have been synthesized and characterized. We demonstrate that the fluorescence properties of these complexes are highly affected by the linking position of the anthracene unit, as only 2 shows fluorescence emission in the blue region. Regarding their biological activity, both ruthenium metallodrugs show interaction with different biological targets such as S-donor amino acids (cysteine) and proteases (cysteine cathepsin B). Moreover, 1 and 2 show in vitro cytotoxicity against HL-60 cancer cell line (IC50 = 84.5 and 87.0 mu M for 1 and 2, respectively), with cell death occurring via apoptosis. Further studies have shown that diffusion into cells is the main mechanism of metallodrug uptake. Finally, as a proof of concept, these ruthenium complexes have been successfully encapsulated into MCM-41 and SBA-15 mesoporous silicas using two different incorporation strategies (impregnation and grinding). (C) 2016 Elsevier Inc. All rights reserved.