4-(3-乙炔基苯氧基)苯-1,2-二胺 | 58297-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3-乙炔基苯氧基)苯-1,2-二胺
• 英文名称: 4-(3-ethynylphenoxy)-1,2-phenylenediamine
• 英文别名: 4-(3-ethynylphenoxy)-o-phenylenediamine；4-(3-ethynylphenoxy)orthophenylene diamine；4-(3-Ethynylphenoxy)benzene-1,2-diamine
• CAS: 58297-25-9
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: ZHSBXPTVBMMGNA-UHFFFAOYSA-N

物化性质

• 沸点：
  404.3±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-乙炔基苯氧基)苯-1,2-二胺 以 乙醇 为溶剂， 反应 2.0h， 生成 1-(5-(3-ethynylphenoxy)-1H-benzimidazole-2-yl)-3-methylurea
  参考文献：
  名称：

  New benzimidazole-2-urea derivates as tubulin inhibitors

  摘要：

  Emerging drug resistance and other drawbacks limit tubulin inhibitors' therapeutic applications and developing novel tubulin inhibitors still attracts intensive efforts. We describe the discovery and structure-activity relationship study of a series of benzimidazole-2-urea derivatives as novel β tubulin inhibitors. The representative compound 6o potently suppressed the proliferation of a panel of human cancer cells (NCI-H460, Colo205, K562, A431, HepG2, Hela, MDA-MB-435S) with IC50 values of 0.040, 0.050, 0.006, 0.026, 1.774, 0.452 and 0.052 μM, respectively. Compound 6o obviously inhibited NCI-H460 spindles formation and induced cell cycle arrest at G2/M phase at 0.10 μM. Computational study suggested that 6o interacts with β tubulin in a novel binding mode. Our results suggested that benzimidazole-2-urea derivatives might be promising tubulin inhibitors with novel binding mode for further development.

  DOI：

  10.1016/j.bmcl.2014.07.035
• 作为产物：
  描述：

  3-羟基苯基乙炔 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-(3-乙炔基苯氧基)苯-1,2-二胺
  参考文献：
  名称：

  New benzimidazole-2-urea derivates as tubulin inhibitors

  摘要：

  Emerging drug resistance and other drawbacks limit tubulin inhibitors' therapeutic applications and developing novel tubulin inhibitors still attracts intensive efforts. We describe the discovery and structure-activity relationship study of a series of benzimidazole-2-urea derivatives as novel β tubulin inhibitors. The representative compound 6o potently suppressed the proliferation of a panel of human cancer cells (NCI-H460, Colo205, K562, A431, HepG2, Hela, MDA-MB-435S) with IC50 values of 0.040, 0.050, 0.006, 0.026, 1.774, 0.452 and 0.052 μM, respectively. Compound 6o obviously inhibited NCI-H460 spindles formation and induced cell cycle arrest at G2/M phase at 0.10 μM. Computational study suggested that 6o interacts with β tubulin in a novel binding mode. Our results suggested that benzimidazole-2-urea derivatives might be promising tubulin inhibitors with novel binding mode for further development.

  DOI：

  10.1016/j.bmcl.2014.07.035

文献信息

• Ethynyl-substituted aromatic ortho diamines and method of synthesis
  申请人：The Unites States of America as represented by the Secretary of the Air

  公开号：US03975444A1

  公开（公告）日：1976-08-17

  As new compositions of matter, ethynyl-substituted aromatic ortho-diamines. The compounds are useful as endcapping agents for thermally stable heterocyclic oligomeric compositions.

  作为新的物质组成，乙炔取代的芳香基邻二胺。这些化合物可用作对热稳定的杂环寡聚物组成物的端封剂。
• Bis-ethynyl heterocyclic compositions and method of synthesis
  申请人：The United States of America as represented by the Secretary of the Air

  公开号：US04086232A1

  公开（公告）日：1978-04-25

  Bis-ethynyl quinoxaline compositions are prepared by the condensation reaction of an aromatic diglyoxyl or dibenzil with an ethynyl-substituted aromatic ortho-diamine. The compositions are useful as polymerizable plasticizers for heterocyclic thermoplastic resins in the fabrication of composites. Polymerizable plasticizers are materials that remain fluid and act as a plasticizer during early stages of fabrication and then polymerize to a rigid resin.

  双乙炔喹啉组合物是通过芳香二羟基或二苄基与乙炔取代的芳香邻二胺的缩合反应制备的。这些组合物可用作杂环热塑性树脂的可聚合增塑剂，用于制备复合材料。可聚合增塑剂是在制备的早期阶段保持流动并起增塑作用，然后聚合成为硬质树脂的材料。
• 5-芳基酚-2烷基取代脲苯并咪唑类化合物及 其应用
  申请人：中国科学院广州生物医药与健康研究院

  公开号：CN104876878B

  公开（公告）日：2018-04-27

  本发明公开了一种5‑芳基酚‑2烷基取代脲苯并咪唑类化合物及其应用，所述化合物具有式（Ⅰ）结构。本发明涉及的5‑芳基酚‑2烷基取代脲苯并咪唑类化合物在体外能够显著抑制多种肿瘤细胞的增殖，对肿瘤细胞的微管形成与细胞周期G2/M期的阻滞呈现出剂量依赖性；同时为临床治疗肿瘤提供了新的药物选择。
• Addition curable phenyl-quinoxaline compositions and their synthesis
  申请人：The United States of America as represented by the Secretary of the Air

  公开号：US03966729A1

  公开（公告）日：1976-06-29

  An aromatic bis(o-diamine) is reacted with an aromatic bisbenzil to provide a benzil end-capped quinoxaline oligomer which is then reacted with 4-(3-ethynylphenoxy)orthophenylene diamine to give an ethynyl terminated polyquinoxaline. Because the polyquinoxalines can be cured to provide thermally stable polymer compositions having superior mechanical properties, the compositions are particularly suitable for use in the fabrication of reinforced composite structures.

  一种芳香族双(邻二胺)与芳香族双苯甲酮反应，形成苯甲酮端基的喹噁啉寡聚体，然后与4-(3-乙炔基苯氧基)邻苯二胺反应，形成乙炔端基的聚喹噁啉。由于聚喹噁啉可以固化成具有优异机械性能的热稳定聚合物组合物，因此这些组合物特别适用于制造加强复合结构。
• Bis-ethynyl heterocyclic compositions and method of snythesis
  申请人：The United States of America as represented by the Secretary of the Air

  公开号：US04022746A1

  公开（公告）日：1977-05-10

  Bis-ethynyl quinoxaline compositions are prepared by the condensation reaction of an aromatic diglyoxyl or dibenzil with an ethynyl-substituted aromatic ortho-diamine. The compositions are useful as polymerizable plasticizers for heterocyclic thermoplastic resins in the fabrication of composites. Polymerizable plasticizers are materials that remain fluid and act as a plasticizer during early stages of fabrication and then polymerize to a rigid resin.

  Bis-ethynyl quinoxaline组合物是通过芳香二羟基或二苄基与乙炔取代的芳香基对位二胺的缩合反应制备而成。这些组合物可用作杂环热塑性树脂的可聚合增塑剂，用于制造复合材料。可聚合增塑剂是在制造早期保持流动并作为增塑剂的材料，然后聚合为硬质树脂。