5-Nitro-benzimidazol-N-essigsaeure-aethylester | 126401-85-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-Nitro-benzimidazol-N-essigsaeure-aethylester
• 英文别名: (5-nitro-benzoimidazol-1-yl)-acetic acid ethyl ester；Ethyl 2-(5-nitrobenzimidazol-1-yl)acetate
• CAS: 126401-85-2
• 化学式: C₁₁H₁₁N₃O₄
• 分子量: 249.226
• InChiKey: SAEQTLMQTGROQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Nitro-benzimidazol-N-essigsaeure-aethylester 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-(5-nitro-1H-benzo[d]imidazol-1-yl)acetohydrazide
  参考文献：
  名称：

  Unique Azolyl Acylhydrazonyl Hybridization of Aloe Emodins to Access Potential Antibacterial Agents

  摘要：

  A type of unique azole‐hybridized acylhydrazonyl aloe emodins (AAEs) were developed as new antibacterial agents for combating bacterial infections. Some target AAEs showed strong antibacterial activities, especially, tetrazolylthioether AAE 27a exhibited broad antibacterial spectrum with 16—256 folds and 8—64 folds more active antibacterial efficacy than the reference drugs aloe emodin and norfloxacin, respectively. Tetrazolylthioether AAE 27a also gave low hemolysis and cytotoxicity, as well as favorable bioavailability. Preliminary mechanism explorations revealed that tetrazolylthioether AAE 27a could cause bacterial membrane depolarization and damage the cell membrane, resulting in nucleic acid leakage. Moreover, compound 27a could intercalate into DNA to impede its replication and form supramolecular 27a‐DNA gyrase complex to disturb the function of DNA gyrase. These findings would provide valuable insights for the further exploration of azolyl acylhydrazonyl aloe emodins as new potential antibacterial candidates.

  DOI：

  10.1002/cjoc.202400160
• 作为产物：
  描述：

  溴乙酸乙酯 、 6-硝基苯并咪唑 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 5-Nitro-benzimidazol-N-essigsaeure-aethylester
  参考文献：
  名称：

  Unique Azolyl Acylhydrazonyl Hybridization of Aloe Emodins to Access Potential Antibacterial Agents

  摘要：

  A type of unique azole‐hybridized acylhydrazonyl aloe emodins (AAEs) were developed as new antibacterial agents for combating bacterial infections. Some target AAEs showed strong antibacterial activities, especially, tetrazolylthioether AAE 27a exhibited broad antibacterial spectrum with 16—256 folds and 8—64 folds more active antibacterial efficacy than the reference drugs aloe emodin and norfloxacin, respectively. Tetrazolylthioether AAE 27a also gave low hemolysis and cytotoxicity, as well as favorable bioavailability. Preliminary mechanism explorations revealed that tetrazolylthioether AAE 27a could cause bacterial membrane depolarization and damage the cell membrane, resulting in nucleic acid leakage. Moreover, compound 27a could intercalate into DNA to impede its replication and form supramolecular 27a‐DNA gyrase complex to disturb the function of DNA gyrase. These findings would provide valuable insights for the further exploration of azolyl acylhydrazonyl aloe emodins as new potential antibacterial candidates.

  DOI：

  10.1002/cjoc.202400160

文献信息

• Searcey, M.; Pye, P. L.; Lee, J. B., Synthetic Communications, 1989, vol. 19, # 7,8, p. 1309 - 1316
  作者：Searcey, M.、Pye, P. L.、Lee, J. B.

  DOI：——

  日期：——
• Unique Azolyl Acylhydrazonyl Hybridization of Aloe Emodins to Access Potential Antibacterial Agents
  作者：Yi‐Xin Wang、Zhao Deng、Aisha Bibi、Bo Fang、Cheng‐He Zhou

  DOI：10.1002/cjoc.202400160

  日期：——

  A type of unique azole‐hybridized acylhydrazonyl aloe emodins (AAEs) were developed as new antibacterial agents for combating bacterial infections. Some target AAEs showed strong antibacterial activities, especially, tetrazolylthioether AAE 27a exhibited broad antibacterial spectrum with 16—256 folds and 8—64 folds more active antibacterial efficacy than the reference drugs aloe emodin and norfloxacin, respectively. Tetrazolylthioether AAE 27a also gave low hemolysis and cytotoxicity, as well as favorable bioavailability. Preliminary mechanism explorations revealed that tetrazolylthioether AAE 27a could cause bacterial membrane depolarization and damage the cell membrane, resulting in nucleic acid leakage. Moreover, compound 27a could intercalate into DNA to impede its replication and form supramolecular 27a‐DNA gyrase complex to disturb the function of DNA gyrase. These findings would provide valuable insights for the further exploration of azolyl acylhydrazonyl aloe emodins as new potential antibacterial candidates.