2-(5-methoxy-1H-benzo[d]imidazol-2-ylthio)-N-(4-nitrophenyl)acetamide | 356776-32-4

• 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-(5-methoxy-1H-benzo[d]imidazol-2-ylthio)-N-(4-nitrophenyl)acetamide
• 英文别名: 2-[(6-methoxy-1H-benzimidazol-2-yl)sulfanyl]-N-(4-nitrophenyl)acetamide
• CAS: 356776-32-4
• 化学式: C₁₆H₁₄N₄O₄S
• mdl: MFCD02321063
• 分子量: 358.378
• InChiKey: LYQDSNOFTIZWAX-UHFFFAOYSA-N

物化性质

• 溶解度：
  二甲基亚砜：≥30mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  6

制备方法与用途

生物活性

AG-09/1 是一种特异性甲酰基肽受体 1 (FPR1) 激动剂。FPR 在宿主防御中起着重要作用。

靶点

• FPR1

体外研究

N-形式基肽通过 G 蛋白偶联受体（FPR）激活吞噬细胞。FPR1 是首个被克隆的 FPR，编码 fMLF 的高亲和力受体。

反应信息

• 作为产物：
  描述：

  4-甲氧基邻苯二胺 在 盐酸 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 4.0h， 生成 2-(5-methoxy-1H-benzo[d]imidazol-2-ylthio)-N-(4-nitrophenyl)acetamide
  参考文献：
  名称：

  Synthesis and evaluation of novel benzimidazole derivatives as antimicrobial agents

  摘要：

  Benzimidazole analogs bearing electron-withdrawing as well as electron-donating substituent were synthesized to achieve bioactive molecules with significant antimicrobial property. The desired compounds were prepared by multi-step synthesis process. The formation of intermediates and their corresponding derivatives (III (1-13) ) was confirmed by spectral characterization such as H-1 NMR, C-13 NMR, mass spectra, IR, and elemental analysis. The compounds were screened for their antimicrobial properties against a broad panel of Gram-positive and Gram-negative bacteria as well as fungi. From the SAR study data, it was observed that the derivatives with electron-withdrawing functional groups were more bioactive than that with electron-donating functional groups.

  DOI：

  10.1007/s00044-013-0732-z