5-[(2-methyl-5-nitro-1H-benzimidazol-1-yl)methyl]-1,3,4-thiadiazol-2(3H)-thione | 913706-14-6

• 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: 5-[(2-methyl-5-nitro-1H-benzimidazol-1-yl)methyl]-1,3,4-thiadiazol-2(3H)-thione
• CAS: 913706-14-6
• 化学式: C₁₁H₉N₅O₂S₂
• 分子量: 307.357
• InChiKey: DCNZZDCEUQSUOR-UHFFFAOYSA-N

物化性质

• 熔点：
  235 °C(Solv: methanol (67-56-1))
• 沸点：
  534.6±56.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  89.64
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-[(2-methyl-5-nitro-1H-benzimidazol-1-yl)methyl]-1,3,4-thiadiazol-2(3H)-thione 、 溴乙酸乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以84%的产率得到ethyl 2-[5-((2-methyl-5-nitro-1H-benzimidazol-1-yl)methyl)-1,3,4-thiadiazol-2-yl-thio]acetate
  参考文献：
  名称：

  Synthesis and antitumor activity of 1-substituted-2-methyl-5-nitrobenzimidazoles

  摘要：

  Different substituents were introduced in position 1 of 2-methyl-5(6)-nitro-1H-benzimidazole (2) in order to obtain different side chains having different heterocyclic compounds, for example, thiadiazoles (5-7), tetrazoles (8, 9a, b), triazoles (11-13), thiazoles (14a-e), triazines (10, 16, 17), and imidazoles (18a-c). The antitumor effect of compounds 1, 2, 2a, 4, 5, 7, 8, 9a, 10, 13, 14a, 15, 16, and 18c was studied against breast cancer (MCF7) and compounds 2 [IC50 = 4.52 mu g] and 7 [IC50 = 8.29 mu g] were found to be active. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.033
• 作为产物：
  描述：

  2-甲基苯并咪唑 在 硫酸 、 硝酸 、 sodium hydride 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 5-[(2-methyl-5-nitro-1H-benzimidazol-1-yl)methyl]-1,3,4-thiadiazol-2(3H)-thione
  参考文献：
  名称：

  Synthesis and antitumor activity of 1-substituted-2-methyl-5-nitrobenzimidazoles

  摘要：

  Different substituents were introduced in position 1 of 2-methyl-5(6)-nitro-1H-benzimidazole (2) in order to obtain different side chains having different heterocyclic compounds, for example, thiadiazoles (5-7), tetrazoles (8, 9a, b), triazoles (11-13), thiazoles (14a-e), triazines (10, 16, 17), and imidazoles (18a-c). The antitumor effect of compounds 1, 2, 2a, 4, 5, 7, 8, 9a, 10, 13, 14a, 15, 16, and 18c was studied against breast cancer (MCF7) and compounds 2 [IC50 = 4.52 mu g] and 7 [IC50 = 8.29 mu g] were found to be active. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.033