1-methyl-2-(bromomethyl)-4,7-dimethoxybenzimidazole | 99922-37-9

• 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: 1-methyl-2-(bromomethyl)-4,7-dimethoxybenzimidazole
• 英文别名: 2-(Bromomethyl)-1-methyl-1H-benzimidazole-4,7-diol；2-(bromomethyl)-1-methylbenzimidazole-4,7-diol
• CAS: 99922-37-9
• 化学式: C₉H₉BrN₂O₂
• 分子量: 257.087
• InChiKey: WWIHBPPLUFGQPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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-(bromomethyl)-4,7-dimethoxybenzimidazole 在 phosphate buffer 、 potassium chloride 作用下， 反应 1.5h， 生成 1,2-dimethylbenzimidazole-4,7-dione 、 1-methyl-2-(chloromethyl)-4,7-dimethoxybenzimidazole
  参考文献：
  名称：

  Studies of extended quinone methides. The hydrolysis mechanism of 1-methyl-2-(bromomethyl)-4,7-dihydroxybenzimidazole

  摘要：

  DOI：

  10.1021/jo00354a023

文献信息

• Recognition and cleavage at the DNA major groove
  申请人：——

  公开号：US20030119022A1

  公开（公告）日：2003-06-26

  DNA recognition agents based on the indole-based aziridinyl eneimine and the cyclopent[b]indole methide species are described. The recognition process involved either selective alkylation or intercalating interactions in the major groove. DNA cleavage resulted from phosphate backbone alkylation (hydrolytic cleavage) and N(7)-alkylation (piperidine cleavage). The formation and fate of the eneimine was studied using enriched 13 C NMR spectra and x-ray crystallography. The aziridinyl eneimine specifically alkylates the N(7) position of DNA resulting in direction of the aziridinyl alkylating center to either the 3′- or 5′-phosphate of the alkylated base. The eneimine species forms dimers and trimers that appear to recognize DNA at up to three base pairs. The cyclopent[b]indole quinone methide recognizes the 3′-GT-5′ sequence and alkylates the guanine N(7) and the thymine 6-carbonyl oxygen causing the hydrolytic removal of these bases. New classes of DNA recognition agents have been developed and the utility of 13 C-enrichment and 13 C-NMR to study DNA alkylation reactions is disclosed.

  本文介绍了基于吲唑烯烯胺和环戊[b]吲哚亚甲基物种的DNA识别剂。识别过程涉及到主沟槽中的选择性烷基化或插入作用。磷酸骨架烷基化（水解裂解）和N（7）烷基化（吡啶裂解）导致DNA裂解。使用富集的13C NMR光谱和X射线晶体学研究了烯烯胺的形成和命运。吲唑烯烯胺特异性烷基化DNA的N（7）位，从而将吲唑烯烷基化中心的方向定向到烷基化碱基的3'-或5'-磷酸。烯烯胺物种形成二聚体和三聚体，似乎能够识别DNA的最多三个碱基对。环戊[b]吲哚醌亚甲基物种识别3'-GT-5'序列，并烷基化鸟嘌呤N（7）和胸腺嘧啶6-羰基氧，导致这些碱基的水解去除。开发了新的DNA识别剂类别，并披露了13C富集和13C-NMR用于研究DNA烷基化反应的实用性。
• 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.