3-(2-bromophenylamino)-6-chloropyridazine | 1094223-54-7

• 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: 3-(2-bromophenylamino)-6-chloropyridazine
• 英文别名: N-(2-bromophenyl)-6-chloropyridazin-3-amine
• CAS: 1094223-54-7
• 化学式: C₁₀H₇BrClN₃
• 分子量: 284.543
• InChiKey: AHLCBRSSOUFYNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-bromophenylamino)-6-chloropyridazine 在 溶剂黄146 作用下， 反应 5.0h， 以60%的产率得到6-(2-bromophenylamino)pyridazin-3(2H)-one
  参考文献：
  名称：

  Design, synthesis, and evaluation of anti-inflammatory and ulcerogenicity of novel pyridazinone derivatives

  摘要：

  A series of pyridazinone-containing compounds were designed and synthesized as congeners for diclofenac, the most potent and widely used NSAID. The target compounds were evaluated for their anti-inflammatory activity on rat paw edema inflammation model against diclofenac as a reference compound. Seven of the tested compounds demonstrated more than 50% inhibition of carrageenan-induced rat paw edema at a dose 10 mg/kg. The compounds, 6-(2-bromophenylamino)pyridazin-3(2H)-one 2a and 6-(2,6-dimethylphenylamino)pyridazin-3(2H)-one 2e, displayed 74 and 73.5% inflammation-inhibitory activity, respectively, which is comparable to diclofenac (78.3%) at the same dose level after 4 h. The most active compounds as anti-inflammatory agents, 2a, 2e, and 6a, displayed fewer number of ulcers and milder ulcer score than indomethacin in ulcerogenicity screening.

  DOI：

  10.1007/s00044-011-9895-7
• 作为产物：
  描述：

  3,6-二氯哒嗪 、 2-溴苯胺 以 乙醇 为溶剂， 以77 %的产率得到3-(2-bromophenylamino)-6-chloropyridazine
  参考文献：
  名称：

  使用可转化哒嗪导向基团通过 C-H 激活/1,4-Rh 迁移/双键转移实现不对称 [5+1] 环化

  摘要：

  N-杂环辅助的C-H活化/环化反应为氮杂环的构建和转化提供了新的概念。在这项工作中，我们公开了使用新型可转化哒嗪导向基团 (DG) 的 [5+1] 环化反应。DG 可转化反应模式导致新杂环的构建，同时通过 C–H 活化/1,4-Rh 迁移/双键转移途径转化原始哒嗪导向基团，提供哒嗪骨架[6] ,1- b ]喹唑啉在温和条件下具有良好的底物范围。通过产物的衍生化可以得到多种稠环化合物。还实现了骨架的不对称合成，以提供具有良好立体选择性的对映体产物。

  DOI：

  10.1021/acs.orglett.3c00278

文献信息

• Triazolopyridazine derivatives: Synthesis, cytotoxic evaluation, c-Met kinase activity and molecular docking
  作者：Eman M. Ahmed、Nadia A. Khalil、Azza T. Taher、Rana H. Refaey、Yassin M. Nissan

  DOI：10.1016/j.bioorg.2019.103272

  日期：2019.11

  Novel series of some triazolo[4,3-b]pyridazine derivatives were designed and synthesized. All the newly synthesized compounds were evaluated for their cytotoxic activity at 10−5 M concentration towards 60 cancer cell lines according to USA NCI protocol. Most of the synthesized compounds showed good activity against SR (leukemia) cell panel. The most active compounds, 2f and 4a were subjected for further

  设计并合成了一些新的三唑并[4,3- b ]哒嗪衍生物系列。 根据USA NCI方案，评估所有新合成的化合物在10 -5 M浓度下对60种癌细胞系的细胞毒活性。大多数合成的化合物显示出对SR（白血病）细胞的良好活性。活性最强的化合物2f和4a在5个剂量水平的筛选下进行了进一步评估，并在体外确定了其对c-Met激酶抑制的功效。通过分子对接探索了这些衍生物的结合方式。
• Design, synthesis, and evaluation of anti-inflammatory and ulcerogenicity of novel pyridazinone derivatives
  作者：K. A. M. Abouzid、N. A. Khalil、E. M. Ahmed、A. Esmat、A. M. Al-Abd

  DOI：10.1007/s00044-011-9895-7

  日期：2012.11

  A series of pyridazinone-containing compounds were designed and synthesized as congeners for diclofenac, the most potent and widely used NSAID. The target compounds were evaluated for their anti-inflammatory activity on rat paw edema inflammation model against diclofenac as a reference compound. Seven of the tested compounds demonstrated more than 50% inhibition of carrageenan-induced rat paw edema at a dose 10 mg/kg. The compounds, 6-(2-bromophenylamino)pyridazin-3(2H)-one 2a and 6-(2,6-dimethylphenylamino)pyridazin-3(2H)-one 2e, displayed 74 and 73.5% inflammation-inhibitory activity, respectively, which is comparable to diclofenac (78.3%) at the same dose level after 4 h. The most active compounds as anti-inflammatory agents, 2a, 2e, and 6a, displayed fewer number of ulcers and milder ulcer score than indomethacin in ulcerogenicity screening.
• Asymmetric [5+1] Annulation via C–H Activation/1,4-Rh Migration/Double Bond Shift Using a Transformable Pyridazine Directing Group
  作者：Man Zhu、Yuyao Zhao、Xingwei Li、Bingxian Liu

  DOI：10.1021/acs.orglett.3c00278

  日期：2023.3.24

  azacycles. In this work, we disclose a [5+1] annulation reaction using a novel transformable pyridazine directing group (DG). The DG-transformable reaction mode led to the construction of a new heterocyclic ring accompanied by transformation of the original pyridazine directing group via a C–H activation/1,4-Rh migration/double bond shift pathway, affording the skeleton of pyridazino[6,1-b]quinazolines

  N-杂环辅助的C-H活化/环化反应为氮杂环的构建和转化提供了新的概念。在这项工作中，我们公开了使用新型可转化哒嗪导向基团 (DG) 的 [5+1] 环化反应。DG 可转化反应模式导致新杂环的构建，同时通过 C–H 活化/1,4-Rh 迁移/双键转移途径转化原始哒嗪导向基团，提供哒嗪骨架[6] ,1- b ]喹唑啉在温和条件下具有良好的底物范围。通过产物的衍生化可以得到多种稠环化合物。还实现了骨架的不对称合成，以提供具有良好立体选择性的对映体产物。