N'-benzoyl-2-(5-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carbohydrazide | 1296210-46-2

• 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: N'-benzoyl-2-(5-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carbohydrazide
• 英文别名: N'-benzoyl-2-(5-nitro-2-thienyl)-1H-benzimidazole-5-carbohydrazide；N'-benzoyl-2-(5-nitrothiophen-2-yl)-3H-benzimidazole-5-carbohydrazide
• CAS: 1296210-46-2
• 化学式: C₁₉H₁₃N₅O₄S
• 分子量: 407.409
• InChiKey: GURXKDBQBYXUSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  161
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-硝基噻吩-2-甲醛 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 硝基苯 、 苯 为溶剂， 反应 56.5h， 生成 N'-benzoyl-2-(5-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carbohydrazide
  参考文献：
  名称：

  Synthesis and biological evaluation of benzimidazole-5-carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents

  摘要：

  A series of N'-substituted-2-(5-nitrofuran or 5-nitrothiophen-2-yl)-3H-benzo[d]imidazole-5-carbohydrazide derivatives were synthesized and investigated for their abilities to inhibit beta-hematin formation, hemoglobin hydrolysis and in vivo for their antimalarial efficacy in rodent Plasmodium berghei. Selected analogues were screened for their antitubercular activity against sensitive MTB H(37)Rv and multidrug-resistant MDR-MTB strains, and cytotoxic activity against a panel of human tumor cell lines and two non-tumourogenic cell lines. Compounds 3a, 5a, f, 6g were the most promising as inhibitors of beta-hematin formation, however, their effect as inhibitors of hemoglobin hydrolysis were marginal. The most active compounds to emerge from the in vitro and in vivo murine studies were 3a and 6i, suggesting an antimalarial activity via inhibition of beta-hematin formation and are as efficient as chloroquine. The cytotoxic and antitubercular activities of the present compounds were not comparable with those of the standard drugs employed. But, however, compound 5b showed better antitubercular activity compared to rifampin against multidrug-resistant MDR-MTB strains. Compounds 3a, 6i and 5b showed a good safety index. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.050

文献信息

• Synthesis and biological evaluation of benzimidazole-5-carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents
  作者：José Camacho、Arthur Barazarte、Neira Gamboa、Juan Rodrigues、Rosario Rojas、Abraham Vaisberg、Robert Gilman、Jaime Charris

  DOI：10.1016/j.bmc.2011.01.050

  日期：2011.3

  A series of N'-substituted-2-(5-nitrofuran or 5-nitrothiophen-2-yl)-3H-benzo[d]imidazole-5-carbohydrazide derivatives were synthesized and investigated for their abilities to inhibit beta-hematin formation, hemoglobin hydrolysis and in vivo for their antimalarial efficacy in rodent Plasmodium berghei. Selected analogues were screened for their antitubercular activity against sensitive MTB H(37)Rv and multidrug-resistant MDR-MTB strains, and cytotoxic activity against a panel of human tumor cell lines and two non-tumourogenic cell lines. Compounds 3a, 5a, f, 6g were the most promising as inhibitors of beta-hematin formation, however, their effect as inhibitors of hemoglobin hydrolysis were marginal. The most active compounds to emerge from the in vitro and in vivo murine studies were 3a and 6i, suggesting an antimalarial activity via inhibition of beta-hematin formation and are as efficient as chloroquine. The cytotoxic and antitubercular activities of the present compounds were not comparable with those of the standard drugs employed. But, however, compound 5b showed better antitubercular activity compared to rifampin against multidrug-resistant MDR-MTB strains. Compounds 3a, 6i and 5b showed a good safety index. (C) 2011 Elsevier Ltd. All rights reserved.