2-methyl-1H-benzimidazole-5-carbohydrazide | 713-17-7

• 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-methyl-1H-benzimidazole-5-carbohydrazide
• 英文别名: 2-methyl-3H-benzimidazole-5-carbohydrazide
• CAS: 713-17-7
• 化学式: C₉H₁₀N₄O
• mdl: MFCD01451511
• 分子量: 190.205
• InChiKey: PAHSLRSDDHOJQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  83.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-1H-benzimidazole-5-carbohydrazide 、 3,4-二甲氧基苯甲醛 在 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 10.0h， 以83%的产率得到N'-[(E)-(3,4-dimethoxyphenyl)methylidene]-2-methyl-1H-benzimidazole-5-carbohydrazide
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-methyl-1H-benzimidazole-5-carbohydrazides derivatives as modifiers of redox homeostasis of Trypanosoma cruzi

  摘要：

  Twelve novel benzimidazole derivatives were synthesized and their in vitro activities against epimastigotes of Trypanosoma cruzi were evaluated. Two derivatives (6 and 7), which have 4-hydroxy-3-methoxyphenyl moiety in their structures, proved to be the most active in inhibiting the parasite growth. Compound 6 showed a trypanocidal activity higher than benznidazole (IC50 = 5 mu M and 7.5 mu M, respectively) and less than nifurtimox (IC50 = 3.6 mu M). In addition, the ability of 6 and 7 to modify the redox homeostasis in T cruzi epimastigote was studied; cysteine and glutathione increased in parasites exposed to both compounds, whereas trypanothione only increased with 7 treatment. These results suggest that the decrease in viability of T. cruzi may be attributed to the change in cellular redox balance caused by compound 6 or 7. Furthermore, compounds 6 and 7 showed CC50 values of 160.64 and 160.66 mu M when tested in mouse macrophage cell line J774 and selectivity indexes (macrophage/parasite) of 32 and 20.1, respectively. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.06.013
• 作为产物：
  描述：

  2-甲基-3H-苯并咪唑-5-羧酸 在 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 2-methyl-1H-benzimidazole-5-carbohydrazide
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-methyl-1H-benzimidazole-5-carbohydrazides derivatives as modifiers of redox homeostasis of Trypanosoma cruzi

  摘要：

  Twelve novel benzimidazole derivatives were synthesized and their in vitro activities against epimastigotes of Trypanosoma cruzi were evaluated. Two derivatives (6 and 7), which have 4-hydroxy-3-methoxyphenyl moiety in their structures, proved to be the most active in inhibiting the parasite growth. Compound 6 showed a trypanocidal activity higher than benznidazole (IC50 = 5 mu M and 7.5 mu M, respectively) and less than nifurtimox (IC50 = 3.6 mu M). In addition, the ability of 6 and 7 to modify the redox homeostasis in T cruzi epimastigote was studied; cysteine and glutathione increased in parasites exposed to both compounds, whereas trypanothione only increased with 7 treatment. These results suggest that the decrease in viability of T. cruzi may be attributed to the change in cellular redox balance caused by compound 6 or 7. Furthermore, compounds 6 and 7 showed CC50 values of 160.64 and 160.66 mu M when tested in mouse macrophage cell line J774 and selectivity indexes (macrophage/parasite) of 32 and 20.1, respectively. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.06.013

文献信息

• New transition metal ion complexes with benzimidazole-5-carboxylic acid hydrazides with antitumor activity
  作者：Shadia A. Galal、Khaled H. Hegab、Ahmed S. Kassab、Mireya L. Rodriguez、Sean M. Kerwin、Abdel-Mo'men A. El-Khamry、Hoda I. El Diwani

  DOI：10.1016/j.ejmech.2008.07.013

  日期：2009.4

  Metal complexes of 2-methyl-1H-benzimidazole-5-carboxylic acid hydrazide (4a; L1) and its Schiff base 2-methyl-N-(propan-2-ylidene)-1H-benzimidazole-5-carbohydrazide (5a; L2) with transition metal ions e.g., copper, silver, nickel, iron and manganese were prepared. The complexes formed were 1:1 or 1:2 M:L complexes and have the structural formulae [Cu(L1)Cl(H2O)]Cl·3H2O (6), [Ag(L1)NO3(H2O)] (7),

  2-甲基-1 H-苯并咪唑-5-羧酸酰肼的金属配合物（4a ; L 1）及其席夫碱2-甲基-N-（丙烷-2-亚烷基）-1 H-苯并咪唑-5-碳酰肼（制备具有过渡金属离子例如铜，银，镍，铁和锰的5a； L 2）。形成的配合物为1：1或1：2 M：L配合物，并具有结构式[Cu（L 1）Cl（H 2 O）] Cl·3H 2 O（6），[Ag（L 1）NO 3（H 2 O）]（7），[Ni（L 1）Cl 2（H 2 O）2 ]·H 2 O（8），[Fe（L 1）Cl 3（H 2 O）]·3H 2 O（9）和[Mn（L 1）2 Cl（H 2 O）用于配体L 1的] Cl·3H 2 O（10）和[Cu（L 2）Cl 2（H 2 O）2 ]·H 2 O（11），[Ag（L 2）2 ] NO 3 ·H 2 O（12），[Ni（L 2）2 Cl 2 ]·5H 2 O（13），[Fe（L 2）2 Cl 2 ]
• Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives
  作者：Chao Cong、Haiyang Wang、Yue Hu、Chen Liu、Siti Ma、Xin Li、Jichao Cao、Shutao Ma

  DOI：10.1016/j.ejmech.2011.04.004

  日期：2011.7

  Novel 4 ''-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4 '' bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the me! gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4 ''-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4 ''-O-(2-alkyl) benzimidazolyl derivatives. (C) 2011 Elsevier Masson SAS. All rights reserved.