1,3-bis-(4-iodo-phenyl)-triazene | 62807-94-7

• 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-(4-iodo-phenyl)-triazene
• 英文别名: 4.4'-Dijod-diazoaminobenzol；1,3-Bis-(4-jod-phenyl)-triazen；1-Triazene, 1,3-bis(4-iodophenyl)-；4-iodo-N-[(4-iodophenyl)diazenyl]aniline
• CAS: 62807-94-7
• 化学式: C₁₂H₉I₂N₃
• 分子量: 449.033
• InChiKey: UNCVHPJIOBOQQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 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：
  3

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-(4-iodo-phenyl)-triazene 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以74%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：

  对碘苯胺 在 SHNC 作用下， 以 水 为溶剂， 反应 17.0h， 以94%的产率得到1,3-bis-(4-iodo-phenyl)-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

• [EN] NITROSATION REAGENTS AND METHODS<br/>[FR] RÉACTIFS ET PROCÉDÉS DE NITROSATION
  申请人：UNIV CALIFORNIA

  公开号：WO2021257849A1

  公开（公告）日：2021-12-23

  Provided are compounds that can find use as nitrosation reagents. Provided are nitrosation methods that include reacting a substrate with one of the provided nitrosation reagents and thereby generating a nitrosation product. Provided are kits including a nitrosation reagent. Provided are compositions wherein the nitrosation reagent is enriched in the 15N isotope.

  提供了可用作亚硝化试剂的化合物。提供了包括将底物与提供的亚硝化试剂之一反应，从而生成亚硝化产物的亚硝化方法。提供了包含亚硝化试剂的试剂盒。提供了其中亚硝化试剂富集在15N同位素的组合物。
• Synthesis of 1,3-Diaryltriazenes and Azo Dyes from Aryl Amines Using N-Nitrososulfonamides
  作者：Ryan D. Baxter、Mahshid Yaghoubi

  DOI：10.1055/a-1969-4050

  日期：——

  New methods for the synthesis of 1,3-diaryltriazenes and azo dyes from aryl amines are reported. Both methods involve the formation of aryl diazonium intermediates via the transnitrosation of aryl amines with N-nitrososulfonamides. Each two-step transformation may be performed in one reaction vessel at room temperature with no precautions taken to exclude air or moisture. Several triazene and azo dye

  报道了从芳基胺合成 1,3-二芳基三氮烯和偶氮染料的新方法。这两种方法都涉及通过芳基胺与N -亚硝基磺酰胺的亚硝化反应形成芳基重氮中间体。每个两步转化可在室温下在一个反应​​容器中进行，无需采取任何措施排除空气或水分。这里首次报道了几种三氮烯和偶氮染料结构，证明了在温和条件下操作两步反应序列的实用性。
• Hantzsch; Perkin, Chemische Berichte, 1897, vol. 30, p. 1413
  作者：Hantzsch、Perkin

  DOI：——

  日期：——
• VERNIN G.; SIV C.; METZGER J.; PARKANYI C., SYNTHESIS, 1977, NO 10, 691-
  作者：VERNIN G.、 SIV C.、 METZGER J.、 PARKANYI C.

  DOI：——

  日期：——