2-(1H-苯并咪唑-1-基甲氧基)乙醇 | 46277-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(1H-苯并咪唑-1-基甲氧基)乙醇
• 英文名称: 1-(2-hydroxyethoxymethyl)-benzimidazole
• 英文别名: 2-benzoimidazol-1-ylmethoxy-ethanol；2-(1H-benzimidazol-1-ylmethoxy)ethanol；2-(benzimidazol-1-ylmethoxy)ethanol
• CAS: 46277-27-4
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: CEPOBBMKTRLNKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-苯并咪唑-1-基甲氧基)乙醇 在 4-二甲氨基吡啶 、 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 21.0h， 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：

  1-(2-acetoxyethoxymethyl)-benzimidazole 在 ammonium hydroxide 作用下， 反应 1.5h， 以75%的产率得到2-(1H-苯并咪唑-1-基甲氧基)乙醇
  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

文献信息

• Acyclic analogs of nucleosides. Synthesis of hydroxyalkylbenzimidazoles and -benzotriazoles
  作者：A. �. Yavorskii、A. V. Stetsenko、S. G. Zavgorodnii、V. L. Florent'ev

  DOI：10.1007/bf00473325

  日期：1988.2
• 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.
• YAVORSKIJ, A. EH.;STETSENKO, A. V.;ZAVGORODNIJ, S. G.;FLORENTEV, V. L., XIMIYA GETEROTSIKL. SOED.,(1988) N 2, 198-202
  作者：YAVORSKIJ, A. EH.、STETSENKO, A. V.、ZAVGORODNIJ, S. G.、FLORENTEV, V. L.

  DOI：——

  日期：——
• Synthesis of analogs of l-valacyclovir and determination of their substrate activity for the oligopeptide transporter in Caco-2 cells
  作者：Gerda Marie Friedrichsen、Weiqing Chen、Mikael Begtrup、Chao-Pin Lee、Philip L Smith、Ronald T Borchardt

  DOI：10.1016/s0928-0987(02)00047-7

  日期：2002.7

  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.