2-<2-(2-chloroacetamido)ethyl>benzimidazole | 80028-68-8

• 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: 2-<2-(2-chloroacetamido)ethyl>benzimidazole
• 英文别名: N-[2-(1H-Benzoimidazol-2-yl)-ethyl]-2-chloro-acetamide；N-[2-(1H-benzimidazol-2-yl)ethyl]-2-chloroacetamide
• CAS: 80028-68-8
• 化学式: C₁₁H₁₂ClN₃O
• mdl: MFCD00709330
• 分子量: 237.689
• InChiKey: VCSLTUZHPUOJIB-UHFFFAOYSA-N

物化性质

• 熔点：
  221-223 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  563.1±35.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-<2-(2-chloroacetamido)ethyl>benzimidazole 在 sodium t-butanolate 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 以11.5%的产率得到2,3,4,5-tetrahydro-1H-<1,4>diazepino<1,7-a>benzimidazol-4-one
  参考文献：
  名称：

  Convenient and regioselective synthesis of substituted 2,3,4,5-tetrahydro-1H-1,4-diazepino[1,7-a]benzimidazoles

  摘要：

  DOI：

  10.1021/jo00342a046
• 作为产物：
  描述：

  N-(氯乙酰氧基)琥珀酰亚胺 、 2-(2-aminoethyl)benzimidazole dihydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-<2-(2-chloroacetamido)ethyl>benzimidazole
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Structure–Activity Relationships of Potent Noncovalent and Nonpeptidic Cruzain Inhibitors as Anti-Trypanosoma cruzi Agents

  摘要：

  The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (K(i) = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, K(i) = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.

  DOI：

  10.1021/jm401709b

文献信息

• HUFF, J. R.;KING, S. W.;SAARI, W. S., J. ORG. CHEM., 1982, 47, N 3, 582-585
  作者：HUFF, J. R.、KING, S. W.、SAARI, W. S.

  DOI：——

  日期：——
• Convenient and regioselective synthesis of substituted 2,3,4,5-tetrahydro-1H-1,4-diazepino[1,7-a]benzimidazoles
  作者：Joel R. Huff、Stella W. King、Walfred S. Saari

  DOI：10.1021/jo00342a046

  日期：1982.1
• Synthesis, Biological Evaluation, and Structure–Activity Relationships of Potent Noncovalent and Nonpeptidic Cruzain Inhibitors as Anti-<i>Trypanosoma cruzi</i> Agents
  作者：Rafaela S. Ferreira、Marco A. Dessoy、Ivani Pauli、Mariana L. Souza、Renata Krogh、Ana I. L. Sales、Glaucius Oliva、Luiz C. Dias、Adriano D. Andricopulo

  DOI：10.1021/jm401709b

  日期：2014.3.27

  The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (K(i) = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, K(i) = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.