1-(2-acetoxyethoxymethyl)-benzimidazole | 123414-11-9

• 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-(2-acetoxyethoxymethyl)-benzimidazole
• 英文别名: 2-(Benzimidazol-1-ylmethoxy)ethyl acetate
• CAS: 123414-11-9
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: FDRHCHYCPPLJFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-acetoxyethoxymethyl)-benzimidazole 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 2-(1-benzimidazolemethoxy)ethyl-L-valinate
  参考文献：
  名称：

  Synthesis of analogs of l-valacyclovir and determination of their substrate activity for the oligopeptide transporter in Caco-2 cells

  摘要：

  L-Valacyclovir, a prodrug of acyclovir, is a substrate for the peptide transporter (PepTl) in the intestinal mucosa, which accounts for its higher than expected oral bioavailability. The substrate activity Of L-valacyclovir for PepTl is surprising, particularly when one considers that the molecule has the structural features of a nucleoside rather than a peptide. In an attempt to better understand the structure-transport relationships (STR) for the interactions Of L-valacyclovir with PepTl, analogs of this molecule with structural changes in the guanine moiety were synthesized and their substrate activity for PepTl in Caco-2 cell monolayers was determined. The analogs synthesized include those that had the guanine moiety Of L-valacyclovir substituted with purine, benzimidazole, and 7-azaindole. All three analogs (purine, benzimidazole, and 7-azaindole) exhibited affinity for PepTl in binding studies, but only the purine analog (as the L-valine ester) showed PepT I-associated transcellular transport across Caco-2 cell monolayers. The benzimidazole and 7-azaindole analogs (as their L-valine esters) were rapidly metabolized by esterase when applied to the apical surface of Caco-2 cells, which probably explains their low penetration as the intact prodrugs via PepTl. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00047-7
• 作为产物：
  描述：

  苯并咪唑 在 四氯化锡 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 1-(2-acetoxyethoxymethyl)-benzimidazole
  参考文献：
  名称：

  核苷的无环类似物。羟烷基苯并咪唑和-苯并三唑的合成

  摘要：

  DOI：

  10.1007/bf00473325

文献信息

• Benzimidazole-Derived ATP Analogues as Potential Glutamine Synthetase Inhibitors
  作者：Babalwa S. B. Gxoyiya、Perry T. Kaye、Colin Kenyon

  DOI：10.1080/00397910903289263

  日期：2010.8.5

  A series of mono- and dihydroxyalkyl- and -alkyloxybenzimidazoles and their phosphorylated derivatives have been prepared as adenosine triphoshate analogues for investigation as potential M. Tb. glutamine synthetase inhibitors.