2-(4-methoxyphenylazo)pyridine | 79917-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-methoxyphenylazo)pyridine
• 英文别名: (4-Methoxyphenyl)-pyridin-2-yldiazene
• CAS: 79917-49-0
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: DOFFHXJRDOMZHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [RuCl2(benzene)]2 、 ammonium hexafluorophosphate 、 2-(4-methoxyphenylazo)pyridine 以 甲醇 为溶剂， 反应 28.0h， 以25%的产率得到
  参考文献：
  名称：

  Cytotoxicity of η-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters

  摘要：

  A new series of amphiphilic eta(6)-areneruthenium(II) compounds containing phenylazo ligands (group I: compounds la, 1b, 2a and 2b) and phenyloxadiazole ligands (group II: compounds 3a, 3b, 4a and 4b) were synthesized and characterized for their anti-glioblastoma activity. The effects of the amphiphilic eta(6)-areneruthenium(II) complexes on the viability of three human glioblastoma cell lines, U251, U87MG and T98G, were evaluated. The azo-derivative ruthenium complexes (group I) showed high cytotoxicity to all cell lines, whilst most oxadiazole-derivative complexes (group II) were less cytotoxic, except for compound 4a. The cationic complexes 2a, 2b and 4b were more cytotoxic than the neutral complexes. Compounds 2a and 2b caused a significant reduction in the percentage of cells in the G0/G1 phase, with concomitant increases in the G2/M phase and fragmented DNA in the T98G cell line. The eta(6)-areneruthenium(11) compounds were also tested in cell lines that overexpress the multidrug ABC transporters P-gp, MRP1 and ABCG2. Compounds 2b and 4a were substrates for the P-gp protein, with resistance indexes of 8.6 and 1.9, respectively. Compound 2b was also a substrate for ABCG2 and MRP1 proteins, with lower resistance indexes (1.8 and 1.6, respectively). The contribution of multidrug ABC transporters to the cytotoxicity of compound 2b in T98G cells was evidenced, since verapamil (a characteristic inhibitor of MRP1) increased the cytotoxicity of compound 2b at concentrations up to 20 mu mol L-1, whilst GP120918 and Ko143 (specific inhibitors of P-gp and ABCG2, respectively) had no significant effect. In addition, we showed that compound 2b interacts with glutathione (GSH), which could explain its cellular efflux by MRP1. Our results showed that the amphiphilic eta(6)-areneruthenium(II) complexes are promising anti-glioblastoma compounds, especially compound 2b, which was cytotoxic for all three cell lines, although it is transported by the three main multidrug ABC transporters. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.026
• 作为产物：
  描述：

  2-肼吡啶 在 硫酸 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 21.5h， 生成 2-(4-methoxyphenylazo)pyridine
  参考文献：
  名称：

  Cytotoxicity of η-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters

  摘要：

  A new series of amphiphilic eta(6)-areneruthenium(II) compounds containing phenylazo ligands (group I: compounds la, 1b, 2a and 2b) and phenyloxadiazole ligands (group II: compounds 3a, 3b, 4a and 4b) were synthesized and characterized for their anti-glioblastoma activity. The effects of the amphiphilic eta(6)-areneruthenium(II) complexes on the viability of three human glioblastoma cell lines, U251, U87MG and T98G, were evaluated. The azo-derivative ruthenium complexes (group I) showed high cytotoxicity to all cell lines, whilst most oxadiazole-derivative complexes (group II) were less cytotoxic, except for compound 4a. The cationic complexes 2a, 2b and 4b were more cytotoxic than the neutral complexes. Compounds 2a and 2b caused a significant reduction in the percentage of cells in the G0/G1 phase, with concomitant increases in the G2/M phase and fragmented DNA in the T98G cell line. The eta(6)-areneruthenium(11) compounds were also tested in cell lines that overexpress the multidrug ABC transporters P-gp, MRP1 and ABCG2. Compounds 2b and 4a were substrates for the P-gp protein, with resistance indexes of 8.6 and 1.9, respectively. Compound 2b was also a substrate for ABCG2 and MRP1 proteins, with lower resistance indexes (1.8 and 1.6, respectively). The contribution of multidrug ABC transporters to the cytotoxicity of compound 2b in T98G cells was evidenced, since verapamil (a characteristic inhibitor of MRP1) increased the cytotoxicity of compound 2b at concentrations up to 20 mu mol L-1, whilst GP120918 and Ko143 (specific inhibitors of P-gp and ABCG2, respectively) had no significant effect. In addition, we showed that compound 2b interacts with glutathione (GSH), which could explain its cellular efflux by MRP1. Our results showed that the amphiphilic eta(6)-areneruthenium(II) complexes are promising anti-glioblastoma compounds, especially compound 2b, which was cytotoxic for all three cell lines, although it is transported by the three main multidrug ABC transporters. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.026

文献信息

• [EN] CATIONIC DIRECT DYES<br/>[FR] COLORANTS DIRECTS CATIONIQUES
  申请人：BASF SE

  公开号：WO2016146813A1

  公开（公告）日：2016-09-22

  The invention relates to cationic direct dyes of the formula I (1), wherein m and n are independently from each other 0 or 1, D is an aromatic or a cationic heteroaromatic group, which are further specified, K is an aromatic or heteroaromatic group, E1 and E2 are independently from each other =CH- or =N-, An is an anion and a is a number from 1 to 6 and R1 and R2 are independently from each other and further specified. The compounds show washfastness at hair-dying.

  这项发明涉及公式I（1）的阳离子直接染料，其中m和n分别独立于0或1，D是芳香或阳离子杂芳基，进一步具体说明，K是芳香或杂芳基，E1和E2分别独立于=CH-或=N-，An是阴离子，a是1到6之间的数字，R1和R2分别独立于彼此并进一步具体说明。这些化合物在染发时表现出良好的耐洗性。
• CATIONIC DIRECT DYES
  申请人：BASF SE

  公开号：EP3271423A1

  公开（公告）日：2018-01-24
• Cationic Direct Dyes
  申请人：BASF SE

  公开号：US20180244924A1

  公开（公告）日：2018-08-30

  The invention relates to cationic direct dyes of the formula I (1), wherein m and n are independently from each other 0 or 1, D is an aromatic or a cationic heteroaromatic group, which are further specified, K is an aromatic or heteroaromatic group, E 1 and E 2 are independently from each other ═CH— or ═N—, An is an anion and a is a number from 1 to 6 and R 1 and R 2 are independently from each other and further specified. The compounds show washfastness at hair-dying.
• US7407516B2
  申请人：——

  公开号：US7407516B2

  公开（公告）日：2008-08-05
• Cytotoxicity of η-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters
  作者：Jaqueline Pazinato、Otávio M. Cruz、Karine P. Naidek、Amanda R.A. Pires、Eduard Westphal、Hugo Gallardo、Hélène Baubichon-Cortay、Maria E.M. Rocha、Glaucia R. Martinez、Sheila M.B. Winnischofer、Attilio Di Pietro、Herbert Winnischofer

  DOI：10.1016/j.ejmech.2018.02.026

  日期：2018.3

  A new series of amphiphilic eta(6)-areneruthenium(II) compounds containing phenylazo ligands (group I: compounds la, 1b, 2a and 2b) and phenyloxadiazole ligands (group II: compounds 3a, 3b, 4a and 4b) were synthesized and characterized for their anti-glioblastoma activity. The effects of the amphiphilic eta(6)-areneruthenium(II) complexes on the viability of three human glioblastoma cell lines, U251, U87MG and T98G, were evaluated. The azo-derivative ruthenium complexes (group I) showed high cytotoxicity to all cell lines, whilst most oxadiazole-derivative complexes (group II) were less cytotoxic, except for compound 4a. The cationic complexes 2a, 2b and 4b were more cytotoxic than the neutral complexes. Compounds 2a and 2b caused a significant reduction in the percentage of cells in the G0/G1 phase, with concomitant increases in the G2/M phase and fragmented DNA in the T98G cell line. The eta(6)-areneruthenium(11) compounds were also tested in cell lines that overexpress the multidrug ABC transporters P-gp, MRP1 and ABCG2. Compounds 2b and 4a were substrates for the P-gp protein, with resistance indexes of 8.6 and 1.9, respectively. Compound 2b was also a substrate for ABCG2 and MRP1 proteins, with lower resistance indexes (1.8 and 1.6, respectively). The contribution of multidrug ABC transporters to the cytotoxicity of compound 2b in T98G cells was evidenced, since verapamil (a characteristic inhibitor of MRP1) increased the cytotoxicity of compound 2b at concentrations up to 20 mu mol L-1, whilst GP120918 and Ko143 (specific inhibitors of P-gp and ABCG2, respectively) had no significant effect. In addition, we showed that compound 2b interacts with glutathione (GSH), which could explain its cellular efflux by MRP1. Our results showed that the amphiphilic eta(6)-areneruthenium(II) complexes are promising anti-glioblastoma compounds, especially compound 2b, which was cytotoxic for all three cell lines, although it is transported by the three main multidrug ABC transporters. (C) 2018 Elsevier Masson SAS. All rights reserved.