5-cyclohexyloxy-2-carbomethoxyaminobenzimidazole

• 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-cyclohexyloxy-2-carbomethoxyaminobenzimidazole
• 英文别名: methyl N-(6-cyclohexyloxy-1H-benzimidazol-2-yl)carbamate
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: CDZDPRROUQCNAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  5-cyclohexyloxy-2-carbomethoxyaminobenzimidazole 、 甲胺 以 乙醇 为溶剂， 反应 2.0h， 生成 1-(6-cyclohexyloxy-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-氟-2-硝基苯胺 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-cyclohexyloxy-2-carbomethoxyaminobenzimidazole
  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

• 5-Cycloalkyl thio- and oxy-2-carbalkoxyaminobenzimidazoles
  申请人：SmithKline Corporation

  公开号：US04258198A1

  公开（公告）日：1981-03-24

  New anthelmintic compounds, compositions and methods of use are described utilizing 5-cycloalkylthio and oxy-2-carbalkoxyaminobenzimidazole. Methods of preparation involve the reaction of 4-cycloalkylthio- or oxy-o-phenylenediamine with methyl cyanocarbamate in aqueous miscible organic solvents.

  本文介绍了利用5-环烷基硫醚和氧基-2-羧基氨基苯并咪唑提取新的驱虫化合物、组合物和使用方法。制备方法包括将4-环烷基硫醚-或氧基-o-苯二胺与氰基甲酸甲酯在水溶性有机溶剂中反应。
• Methods and compositions using 5-cycloalkylthio- and
  申请人：SmithKline Corporation

  公开号：US04025638A1

  公开（公告）日：1977-05-24

  New anthelmintic compositions and methods of use are described utilizing 5-cycloalkylthio and oxy-2-carbalkoxyaminobenzimidazoles as active ingredients.

  本发明涉及使用5-环烷基硫和氧-2-羧基氨基苯并咪唑作为活性成分的新型驱虫剂组合物及其使用方法。
• US4025638A
  申请人：——

  公开号：US4025638A

  公开（公告）日：1977-05-24
• US4258198A
  申请人：——

  公开号：US4258198A

  公开（公告）日：1981-03-24
• 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.