1,3-bis(3-chloro-4-fluorophenyl)triazene

• 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: 1,3-bis(3-chloro-4-fluorophenyl)triazene
• 英文别名: 3-chloro-N-[(3-chloro-4-fluorophenyl)diazenyl]-4-fluoroaniline
• 化学式: C₁₂H₇Cl₂F₂N₃
• 分子量: 302.11
• InChiKey: BDTSHLRNKZHBOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1,3-bis(3-chloro-4-fluorophenyl)triazene 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以83%的产率得到
  参考文献：
  名称：

  The 1,3-diaryltriazenido(p-cymene)ruthenium(II) complexes with a high in vitro anticancer activity

  摘要：

  1,3-Diatyltriazenes (1) were let to react with [RuCl2(p-cymene)](2) in the presence of trimethylamine to give neutral 1,3-diatyltriazenido(p-cymene)ruthenium(11) complexes, [RuCl(p-cymene)(ArNNNAr)] (2). The molecular composition of the products 2 was confirmed by NMR spectroscopy and mass spectrometry. The structures of the selected complexes were confirmed by a single crystal X-ray analysis. All triazenido-ruthenium complexes were highly cytotoxic against human cervical carcinoma HeLa cells with IC50 below 6 mu M, as determined by a spectrophotometric MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide) method. The most active was [RuCl(p-cymene)(ArNNNAr)] (Ar = 4-Cl-3-(CF3)-C6H3) (2g) with IC50 of 0.103 +/- 0.006 mu M. In comparison with the data for the non-coordinated triazenes 1, the triazenido-ruthenium complexes 2 exhibited up to 560-times higher activity. Three selected complexes were highly cytotoxic also against several tumor cell lines: laryngeal carcinoma HEp-2 cells and their drug-resistant HEp-2 subline (7 T), colorectal carcinoma HCT-116 cells, lung adenocarcinoma H460 cells, and mammary carcinoma MDA-MB-435 cells. The compounds 2g and [RuCl(p-cymene)(ArNNNAr)] (Ar = 4-I-C6H4) (2j) were similarly cytotoxic against parental and drug-resistant cells. Time and dose dependent accumulation of the cells in the S phase of the cell cycle was induced by the compound 2g, triggering apoptosis. Our preliminary results indicate triazenido-ruthenium complexes as promising anticancer drug candidates. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2015.09.005
• 作为产物：
  描述：

  3-氯-4-氟苯胺 在 SHNC 作用下， 以 水 为溶剂， 反应 4.5h， 以86%的产率得到1,3-bis(3-chloro-4-fluorophenyl)triazene
  参考文献：
  名称：

  用六硝基钴酸钠（III）亚硝化。

  摘要：

  Na（3）Co（NO（2））（6）已被研究作为一种新型试剂，用于对各种含氨基官能团的底物进行亚硝化。反应在试剂的水溶液中进行。反应混合物的pH保持在4.3-5范围内。因此，将酰肼转化为相应的酰基叠氮化物，并且与芳烃磺酰基肼的反应提供了芳烃磺酰基叠氮化物。用Na（3）Co（NO（2））（6）处理芳族胺得到1,3-二芳基三氮烯，收率极高; 还观察到最初形成的重氮化合物与富电子芳环的偶联。由于与该试剂形成络合物，因此无法亚硝化脂肪胺。

  DOI：

  10.1021/jo9703820

文献信息

• Nitrosation with Sodium Hexanitrocobaltate(III)
  作者：Bogdan Štefane、Marijan Kočevar、Slovenko Polanc

  DOI：10.1021/jo9703820

  日期：1997.10.1

  been investigated as a new reagent for the nitrosation of various substrates containing an amino functionality. Reactions took place in an aqueous solution of the reagent. The pH of the reaction mixture remained in the range 4.3-5. Thus, hydrazides were transformed to the corresponding acyl azides, and the reactions with arenesulfonyl hydrazines afforded arenesulfonyl azides. Treatment of aromatic

  Na（3）Co（NO（2））（6）已被研究作为一种新型试剂，用于对各种含氨基官能团的底物进行亚硝化。反应在试剂的水溶液中进行。反应混合物的pH保持在4.3-5范围内。因此，将酰肼转化为相应的酰基叠氮化物，并且与芳烃磺酰基肼的反应提供了芳烃磺酰基叠氮化物。用Na（3）Co（NO（2））（6）处理芳族胺得到1,3-二芳基三氮烯，收率极高; 还观察到最初形成的重氮化合物与富电子芳环的偶联。由于与该试剂形成络合物，因此无法亚硝化脂肪胺。
• The 1,3-diaryltriazenido(p-cymene)ruthenium(II) complexes with a high in vitro anticancer activity
  作者：Jure Vajs、Ivana Steiner、Anamaria Brozovic、Andrej Pevec、Andreja Ambriović-Ristov、Marija Matković、Ivo Piantanida、Damijana Urankar、Maja Osmak、Janez Košmrlj

  DOI：10.1016/j.jinorgbio.2015.09.005

  日期：2015.12

  1,3-Diatyltriazenes (1) were let to react with [RuCl2(p-cymene)](2) in the presence of trimethylamine to give neutral 1,3-diatyltriazenido(p-cymene)ruthenium(11) complexes, [RuCl(p-cymene)(ArNNNAr)] (2). The molecular composition of the products 2 was confirmed by NMR spectroscopy and mass spectrometry. The structures of the selected complexes were confirmed by a single crystal X-ray analysis. All triazenido-ruthenium complexes were highly cytotoxic against human cervical carcinoma HeLa cells with IC50 below 6 mu M, as determined by a spectrophotometric MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide) method. The most active was [RuCl(p-cymene)(ArNNNAr)] (Ar = 4-Cl-3-(CF3)-C6H3) (2g) with IC50 of 0.103 +/- 0.006 mu M. In comparison with the data for the non-coordinated triazenes 1, the triazenido-ruthenium complexes 2 exhibited up to 560-times higher activity. Three selected complexes were highly cytotoxic also against several tumor cell lines: laryngeal carcinoma HEp-2 cells and their drug-resistant HEp-2 subline (7 T), colorectal carcinoma HCT-116 cells, lung adenocarcinoma H460 cells, and mammary carcinoma MDA-MB-435 cells. The compounds 2g and [RuCl(p-cymene)(ArNNNAr)] (Ar = 4-I-C6H4) (2j) were similarly cytotoxic against parental and drug-resistant cells. Time and dose dependent accumulation of the cells in the S phase of the cell cycle was induced by the compound 2g, triggering apoptosis. Our preliminary results indicate triazenido-ruthenium complexes as promising anticancer drug candidates. (C) 2015 Elsevier Inc. All rights reserved.