[5-(4-chloro-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester | 43155-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: [5-(4-chloro-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester
• 英文别名: methyl N-[6-(4-chlorophenoxy)-1H-benzimidazol-2-yl]carbamate
• CAS: 43155-39-1
• 化学式: C₁₅H₁₂ClN₃O₃
• 分子量: 317.732
• InChiKey: VALXOLWJSDAGNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  76.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲胺 、 [5-(4-chloro-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester 以 乙醇 为溶剂， 反应 2.0h， 生成 1-(5-(4-chlorophenoxy)-1H-benzimidazol-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：

  5-(4-chlorophenoxy)-2-nitroaniline 在 sodium hydroxide 、 sodium tetrahydroborate 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 23.67h， 生成 [5-(4-chloro-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester
  参考文献：
  名称：

  5-[（o-，m-和p -R）-苯氧基] -2-苯并咪唑氨基甲酸甲酯的合成及光谱性质

  摘要：

  描述了十一种新颖的5-[（o-，m-，p -R）-苯氧基-2-苯并咪唑氨基甲酸酯甲酯，其具有可能的药理活性作为驱虫药。ir，1 H-nmr，13 C-nmr和质谱证实了所有产物的结构。

  DOI：

  10.1002/jhet.5570340307

文献信息

• Synthesis and spectral properties of methyl 5-[(<i>o</i>-,<i>m</i>-, and<i>p</i>-R)-phenoxy]-2-benzimidazolecarbamate
  作者：Eduardo Cortés Cortés、Luis Angel Araluce Anaya

  DOI：10.1002/jhet.5570340307

  日期：1997.5

  The preparation of eleven novel methyl 5-[(o-, m-, p-R)-phenoxy-2-benzimidazolecarbamates with possible pharmacological activity as anthelmintics is described. The structure of all products was corroborated by ir, 1H-nmr, 13C-nmr and mass spectra.

  描述了十一种新颖的5-[（o-，m-，p -R）-苯氧基-2-苯并咪唑氨基甲酸酯甲酯，其具有可能的药理活性作为驱虫药。ir，1 H-nmr，13 C-nmr和质谱证实了所有产物的结构。
• US3965113A
  申请人：——

  公开号：US3965113A

  公开（公告）日：1976-06-22
• 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.