4-(4-acetamidophenoxy)phenylene-1,2-diamine | 29178-60-7

• 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: 4-(4-acetamidophenoxy)phenylene-1,2-diamine
• 英文别名: 4-(4-acetamidophenoxy)-o-phenylenediamine；N-[4-(3,4-diaminophenoxy)phenyl]acetamide
• CAS: 29178-60-7
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: CQCAXLLEEFECJU-UHFFFAOYSA-N

物化性质

• 沸点：
  516.9±45.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-acetamidophenoxy)phenylene-1,2-diamine 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 methyl 5(6)-(4-aminophenoxy)benzimidazole-2-carbamate
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051
• 作为产物：
  描述：

  对乙酰氨基酚 在 sodium dithionite 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-acetamidophenoxy)phenylene-1,2-diamine
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051

文献信息

• Chemical compounds
  申请人：——

  公开号：US20040082583A1

  公开（公告）日：2004-04-29

  Benzimidazole derivatives, which are useful as TIE-2 and/or VEGFR2 inhibitors are described herein. The described invention also includes methods of making such benzimidazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文描述了作为TIE-2和/或VEGFR2抑制剂有用的苯并咪唑衍生物。所述发明还包括制备这种苯并咪唑衍生物的方法，以及在治疗过度增殖性疾病中使用它们的方法。
• CHEMICAL COMPOUNDS
  申请人：Cheung Mui

  公开号：US20070249600A1

  公开（公告）日：2007-10-25

  Benzimidazole derivatives, which are useful as TIE-2 and/or VEGFR2 inhibitors are described herein. The described invention also includes methods of making such benzimidazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文描述了作为TIE-2和/或VEGFR2抑制剂有用的苯并咪唑衍生物。所述发明还包括制备这种苯并咪唑衍生物的方法，以及在治疗过度增生性疾病中使用它们的方法。
• Benzimidazole vascular damaging agents
  申请人：——

  公开号：US20040058972A1

  公开（公告）日：2004-03-25

  Vascular damaging agents composed of substituted 5(6)-substituted benzimidazole-2-carbamates are provided. These agents are useful in the preparation of medicaments for the treatment of diseases involving neovascularisation, particularly for the treatment of solid tumors, macular degeneration, diabetic retinopathy, rheumatoid arthritis, psoriasis, and atherosclerosis. Embodiments include a 5(6)-substituted benzimidazole-2-carbamate of formula I 1 wherein A represents a multi-substituted alkyl group or aromatic ring.

  本发明提供了由取代的 5(6)-取代的苯并咪唑-2-氨基甲酸酯组成的血管损伤剂。这些制剂可用于制备治疗涉及血管新生的疾病的药物，特别是用于治疗实体瘤、黄斑变性、糖尿病视网膜病变、类风湿性关节炎、牛皮癣和动脉粥样硬化。实施方案包括式 I 的 5(6)-取代的苯并咪唑-2-氨基甲酸酯 1 其中 A 代表多取代烷基或芳香环。
• Abuzar, Syed; Sharma, Satyavan; Gupta, Suman, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 12, p. 1274 - 1278
  作者：Abuzar, Syed、Sharma, Satyavan、Gupta, Suman、Misra, Anuradha、Katiyar, J. C.

  DOI：——

  日期：——
• BENZIMIDAZOLE VASCULAR DAMAGING AGENTS
  申请人：Angiogene Pharmaceuticals Ltd

  公开号：EP1140078B1

  公开（公告）日：2007-08-29