1-methyl-2-(chloromethyl)-4,7-dimethoxybenzimidazole | 219829-11-5

• 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: 1-methyl-2-(chloromethyl)-4,7-dimethoxybenzimidazole
• 英文别名: 2-(chloromethyl)-1-methyl-1H-benzimidazole-4,7-diol；NoName_543；2-(chloromethyl)-1-methylbenzimidazole-4,7-diol
• CAS: 219829-11-5
• 化学式: C₉H₉ClN₂O₂
• 分子量: 212.636
• InChiKey: ZHKOZJYAIZDRJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(chloromethyl)-4,7-dimethoxybenzimidazole 在 potassium dichromate 作用下， 以 水 为溶剂， 反应 2.0h， 以78%的产率得到2-(Chloromethyl)-1-methylbenzimidazole-4,7-dione
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of some benzimidazole-4,7-diones as bioreductive anticancer agents

  摘要：

  New benzimidazole-4,7-diones substituted at 2-position were synthesized via a microwave-assisted reaction using 2-chloromethyl-1,5,6-tri-methyl-1H-benzimidazole-4,7-dione 5b as a key intermediate compound. Their cytotoxicity has been evaluated on colon, breast and lung cancer cell lines. The dimer 17 was shown to possess excellent cytotoxicity comparable to that of mitomycin C. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2007.11.020
• 作为产物：
  描述：

  2-(chloromethyl)-4,7-dimethoxy-1-methyl-1H-benzimidazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到1-methyl-2-(chloromethyl)-4,7-dimethoxybenzimidazole
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of some benzimidazole-4,7-diones as bioreductive anticancer agents

  摘要：

  New benzimidazole-4,7-diones substituted at 2-position were synthesized via a microwave-assisted reaction using 2-chloromethyl-1,5,6-tri-methyl-1H-benzimidazole-4,7-dione 5b as a key intermediate compound. Their cytotoxicity has been evaluated on colon, breast and lung cancer cell lines. The dimer 17 was shown to possess excellent cytotoxicity comparable to that of mitomycin C. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2007.11.020

文献信息

• Studies of extended quinone methides. The hydrolysis mechanism of 1-methyl-2-(bromomethyl)-4,7-dihydroxybenzimidazole
  作者：Edward B. Skibo

  DOI：10.1021/jo00354a023

  日期：1986.2
• Formation and fate of benzimidazole-based quinone methides. Influence of pH on quinone methide fate
  作者：Edward B. Skibo

  DOI：10.1021/jo00048a020

  日期：1992.10

  The influence of pH on quinone methide fate was assessed from a comparative hydrolytic study of benzimidazole hydroquinones and their O-methylated analogues. Elimination of a leaving group from the hydroquinones affords the carbocation or the quinone methide depending on the pH. The O-methylated analogues, on the other hand, can only afford the carbocation species. Evidence is presented herein that the quinone methide species is reversibly protonated to afford the carbocation species. The acid dissociation constant for this equilibrium is pK(a) 5.5. Above pH 5.5, the quinone methide species traps both nucleophiles and the proton. Below pH 5.5, the quinone methide species is protonated to afford the carbocation species, which exclusively traps nucleophiles. Therefore, the carbocation acid dissociation constant can be used to predict quinone methide fate as a function of pH.
• Synthesis and cytotoxicity evaluation of some benzimidazole-4,7-diones as bioreductive anticancer agents
  作者：Armand Gellis、Hervé Kovacic、Narimène Boufatah、Patrice Vanelle

  DOI：10.1016/j.ejmech.2007.11.020

  日期：2008.9

  New benzimidazole-4,7-diones substituted at 2-position were synthesized via a microwave-assisted reaction using 2-chloromethyl-1,5,6-tri-methyl-1H-benzimidazole-4,7-dione 5b as a key intermediate compound. Their cytotoxicity has been evaluated on colon, breast and lung cancer cell lines. The dimer 17 was shown to possess excellent cytotoxicity comparable to that of mitomycin C. (C) 2008 Published by Elsevier Masson SAS.