4,6-dichloro-2-(4-nitrobenzylthio)-1H-benzimidazole

• 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: 4,6-dichloro-2-(4-nitrobenzylthio)-1H-benzimidazole
• 英文别名: 4,6-Dichloro-2-(4-nitrobenzylthio)-1h-benzimidazole；4,6-dichloro-2-[(4-nitrophenyl)methylsulfanyl]-1H-benzimidazole
• 化学式: C₁₄H₉Cl₂N₃O₂S
• 分子量: 354.216
• InChiKey: WVXZZOYDOQPSDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  99.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(氯甲基)-4-硝基苯 、 4,6-dichloro-2-mercaptobenzimidazole 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以59%的产率得到4,6-dichloro-2-(4-nitrobenzylthio)-1H-benzimidazole
  参考文献：
  名称：

  Synthesis, and antiprotozoal and antibacterial activities of S-substituted 4,6-dibromo- and 4,6-dichloro-2-mercaptobenzimidazoles

  摘要：

  The synthesis and some germicidal activities in vitro of two congener series of S-substituted 4,6-dihalogeno-2-mercapto-1H-benzimidazoles are reported. There was no substantial difference between antibacterial activities of corresponding 4,6-dichloro- and 4,6-dibromo-derivatives. The present results confirm lower susceptibility to substituted benzimidazoles of Gram-negative compared to Gram-positive bacteria. Minimum inhibitory concentrations (MICs) of a majority of the novel derivatives ranged between 25 and 100 mug/ml for Gram-positive bacteria. The most active compounds (MICs for Gram-positive bacteria: 0.78-50 mug/ml) were 4,6-dichloro-2-(4-nitrobenzylthio)-1H-benzimidazole and 4,6-dibromo-2-(4-nitrobenzylthio)-1H-benzimidazole that were 4-32 times more potent than nitrofurantoin against all Gram-positive bacteria utilized but Escherichia faecalis, against which they were, respectively, 2 and 4 times less potent than nitrofurantoin. Among Gram-negative bacteria used, Stenotrophomonas maltophilia and Bordetella bronchiseptica were most sensitive (as evidenced by a number of MICs less than or equal to 100 mug/ml), whereas Pseudomonas aeruginosa was most resistant to the new benzimidazole derivatives (all MICs > 400 mug/ml). All the new compounds were at least several times more active against Giardia intestinalis (IC50: 0.006-0.053 mug/ml), and a half of them were at least several times more active against Trichomonas vaginalis (IC50: 0.0015-0.182 mug/ml) than metronidazole (IC50: 0.210 and 0.037 mug/ml, respectively), the drug of choice in the treatment of G. intestinalis and T. vaginalis infections. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2003.10.024

文献信息

• Synthesis, and antiprotozoal and antibacterial activities of S-substituted 4,6-dibromo- and 4,6-dichloro-2-mercaptobenzimidazoles
  作者：Mariola Andrzejewska、Lilian Yepez-Mulia、Amparo Tapia、Roberto Cedillo-Rivera、Agnieszka E. Laudy、Bohdan J. Starościak、Zygmunt Kazimierczuk

  DOI：10.1016/j.ejps.2003.10.024

  日期：2004.2

  The synthesis and some germicidal activities in vitro of two congener series of S-substituted 4,6-dihalogeno-2-mercapto-1H-benzimidazoles are reported. There was no substantial difference between antibacterial activities of corresponding 4,6-dichloro- and 4,6-dibromo-derivatives. The present results confirm lower susceptibility to substituted benzimidazoles of Gram-negative compared to Gram-positive bacteria. Minimum inhibitory concentrations (MICs) of a majority of the novel derivatives ranged between 25 and 100 mug/ml for Gram-positive bacteria. The most active compounds (MICs for Gram-positive bacteria: 0.78-50 mug/ml) were 4,6-dichloro-2-(4-nitrobenzylthio)-1H-benzimidazole and 4,6-dibromo-2-(4-nitrobenzylthio)-1H-benzimidazole that were 4-32 times more potent than nitrofurantoin against all Gram-positive bacteria utilized but Escherichia faecalis, against which they were, respectively, 2 and 4 times less potent than nitrofurantoin. Among Gram-negative bacteria used, Stenotrophomonas maltophilia and Bordetella bronchiseptica were most sensitive (as evidenced by a number of MICs less than or equal to 100 mug/ml), whereas Pseudomonas aeruginosa was most resistant to the new benzimidazole derivatives (all MICs > 400 mug/ml). All the new compounds were at least several times more active against Giardia intestinalis (IC50: 0.006-0.053 mug/ml), and a half of them were at least several times more active against Trichomonas vaginalis (IC50: 0.0015-0.182 mug/ml) than metronidazole (IC50: 0.210 and 0.037 mug/ml, respectively), the drug of choice in the treatment of G. intestinalis and T. vaginalis infections. (C) 2003 Elsevier B.V. All rights reserved.