2-(6-chloropyridazine-3-yloxy)benzamide | 1179308-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(6-chloropyridazine-3-yloxy)benzamide
• 英文别名: 2-(6-chloropyridazin-3-yl)oxybenzamide
• CAS: 1179308-66-7
• 化学式: C₁₁H₈ClN₃O₂
• mdl: MFCD13239120
• 分子量: 249.656
• InChiKey: KTMKRYYTZJZCAW-UHFFFAOYSA-N

物化性质

• 沸点：
  480.8±35.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  78.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(6-chloropyridazine-3-yloxy)benzamide 在 溶剂黄146 作用下， 反应 5.0h， 以80%的产率得到2-(6-oxo-1,6-dihydropyridazin-3-yloxy)benzamide
  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 、 水杨酰胺 在 potassium carbonate 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 以70%的产率得到2-(6-chloropyridazine-3-yloxy)benzamide
  参考文献：
  名称：

  3-[(6-Arylamino)pyridazinylamino]benzoic acids: design, synthesis and in vitro evaluation of anticancer activity

  摘要：

  根据 vatalanib（PTK787）的结构设计并合成了一系列新型取代的 3,6-二取代哒嗪类化合物。最终化合物的细胞毒性在 HT-29 结肠癌细胞株上进行了体外测试。带有 4-氯苯胺基的化合物 2a 和 2b 具有最高的细胞毒性活性，IC50 值分别为 15.3 和 3.9 μM。研究发现，最有前途的化合物 2b 对 HT-29 结肠癌细胞株的活性是 vatalanib 的五倍。

  DOI：

  10.1007/s12272-013-0007-8

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.
• 3-[(6-Arylamino)pyridazinylamino]benzoic acids: design, synthesis and in vitro evaluation of anticancer activity
  作者：Khaled A. M. Abouzid、Nadia A. Khalil、Eman M. Ahmed、Khaled Omar Mohamed

  DOI：10.1007/s12272-013-0007-8

  日期：2013.1

  A series of novel substituted 3,6-disubstituted pyridazines based on the structure of vatalanib (PTK787) were designed and synthesized. The cytotoxicity of the final compounds was tested in vitro on HT-29 colon cancer cell line. Compounds 2a and 2b with 4-chlorophenylamino moiety, exerted the highest cytotoxic activity with IC50 values equal to 15.3 and 3.9 μM respectively. The most promising compound, 2b, was found to be about fivefold more active than vatalanib against HT-29 colon cancer cell line.

  根据 vatalanib（PTK787）的结构设计并合成了一系列新型取代的 3,6-二取代哒嗪类化合物。最终化合物的细胞毒性在 HT-29 结肠癌细胞株上进行了体外测试。带有 4-氯苯胺基的化合物 2a 和 2b 具有最高的细胞毒性活性，IC50 值分别为 15.3 和 3.9 μM。研究发现，最有前途的化合物 2b 对 HT-29 结肠癌细胞株的活性是 vatalanib 的五倍。