5-phenoxy-1H-benzo[d]imidazol-2-amine | 55486-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-phenoxy-1H-benzo[d]imidazol-2-amine
• 英文别名: 6-phenoxy-1H-benzimidazol-2-amine
• CAS: 55486-78-7
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: BSJFXXQHLLJOBA-UHFFFAOYSA-N

物化性质

• 沸点：
  463.4±37.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-2-吡啶甲酸 、 5-phenoxy-1H-benzo[d]imidazol-2-amine 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以27%的产率得到3-hydroxy-N-(6-phenoxy-1H-benzo[d]imidazol-2-yl)picolinamide
  参考文献：
  名称：

  [EN] AGRICULTURAL CHEMICALS
  [FR] PRODUITS CHIMIQUES AGRICOLES

  摘要：

  本发明涉及烟酸衍生物，用于治疗植物的真菌性病害。

  公开号：

  WO2019141980A1
• 作为产物：
  描述：

  2-硝基-5-苯氧基苯胺 在 palladium 10% on activated carbon 、 水 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 11.0h， 生成 5-phenoxy-1H-benzo[d]imidazol-2-amine
  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

• Heterocycle-Substituted Cyclic Urea Derivatives, Preparation Thereof And Pharmaceutical Use Thereof As Kinase Inhibitors
  申请人：Strobel Hartmut

  公开号：US20070259891A1

  公开（公告）日：2007-11-08

  The disclosure relates to compounds of formula (I): wherein Y, Y 1 , Yo, R1, R 2 , R 2 ′, p, R3, R 3 ′, A, B and Y 2 have the meanings given in the description, and to salts thereof, pharmaceutical compositions comprising said compounds and use thereof as protein kinase inhibitors.

  本披露涉及式(I)的化合物：其中Y，Y1，Yo，R1，R2，R2′，p，R3，R3′，A，B和Y2具有描述中给出的含义，以及其盐，包含该化合物的制药组合物以及其作为蛋白激酶抑制剂的用途。
• [EN] AGRICULTURAL CHEMICALS<br/>[FR] PRODUITS CHIMIQUES AGRICOLES
  申请人：GLOBACHEM NV

  公开号：WO2019141980A1

  公开（公告）日：2019-07-25

  The present invention relates to picolinic acid derivatives that are useful in treating fungal diseases ofplants.

  本发明涉及烟酸衍生物，用于治疗植物的真菌性病害。
• New benzimidazole-2-urea derivates as tubulin inhibitors
  作者：Wenna Wang、Dexin Kong、Huimin Cheng、Li Tan、Zhang Zhang、Xiaoxi Zhuang、Huoyou Long、Yang Zhou、Yong Xu、Xiaohong Yang、Ke Ding

  DOI：10.1016/j.bmcl.2014.07.035

  日期：2014.9

  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.