(6-benzyloxy-1H-benzimidazol-2-yl)carbamic acid methyl ester | 54029-21-9

• 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: (6-benzyloxy-1H-benzimidazol-2-yl)carbamic acid methyl ester
• 英文别名: Carbamic acid, (5-(phenylmethoxy)-1H-benzimidazol-2-yl)-, methyl ester；methyl N-(6-phenylmethoxy-1H-benzimidazol-2-yl)carbamate
• CAS: 54029-21-9
• 化学式: C₁₆H₁₅N₃O₃
• 分子量: 297.313
• InChiKey: XVPRZCQQEOPOEX-UHFFFAOYSA-N

物化性质

• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (6-benzyloxy-1H-benzimidazol-2-yl)carbamic acid methyl ester 、 甲胺 以 乙醇 为溶剂， 反应 2.0h， 生成 1-methyl-3-(6-phenylmethoxy-1H-benzimidazol-2-yl)urea
  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：

  4-苄氧基-2-硝基乙酰苯胺) 在 盐酸 、 sodium dithionite 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 73.5h， 生成 (6-benzyloxy-1H-benzimidazol-2-yl)carbamic acid methyl ester
  参考文献：
  名称：

  Bera, Tanmoy; Belsare, D. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 6, p. 370 - 372

  摘要：

  DOI：

文献信息

• 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.
• Bera, Tanmoy; Belsare, D. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 6, p. 370 - 372
  作者：Bera, Tanmoy、Belsare, D. P.

  DOI：——

  日期：——