1-methyl-N-(5-nitro-1,3-thiazol-2-yl)-1H-benzimidazole-6-carboxamide | 1367068-74-3

• 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: 1-methyl-N-(5-nitro-1,3-thiazol-2-yl)-1H-benzimidazole-6-carboxamide
• 英文别名: 3-methyl-N-(5-nitro-1,3-thiazol-2-yl)benzimidazole-5-carboxamide
• CAS: 1367068-74-3
• 化学式: C₁₂H₉N₅O₃S
• 分子量: 303.301
• InChiKey: MVURSKCCQNIOCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(甲基氨基)-4-硝基苯羧酸甲酯 在 盐酸 、 palladium on activated charcoal 、 水 、 氢气 、 N,N'-羰基二咪唑 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 1-methyl-N-(5-nitro-1,3-thiazol-2-yl)-1H-benzimidazole-6-carboxamide
  参考文献：
  名称：

  Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids

  摘要：

  A series of a novel hybrid compounds between nitazoxanide and N-methylbenzimidazole were synthesized starting from the corresponding N-methyl-2-nitroanilines. The new hybrid compounds (1-13) were evaluated in vitro against Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis. NTZ, MTZ and ABZ were used as drug standards. Experimental evaluations revealed all of the new compounds (1-13) were active and showed strong activity against the three protozoa, particularly with E. histolytica where the IC50 values ranged between 3 and 69 nM.Overall, compounds 2, 5, 7, 8, 9, 11 and 12 stood out with values lower than 87 nM for all three protozoa, comparatively better than the reference drugs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.011

文献信息

• Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids
  作者：Olivia Soria-Arteche、Alicia Hernández-Campos、Lilián Yépez-Mulia、Pedro Josué Trejo-Soto、Francisco Hernández-Luis、Jorge Gres-Molina、Luis A. Maldonado、Rafael Castillo

  DOI：10.1016/j.bmcl.2013.10.011

  日期：2013.12

  A series of a novel hybrid compounds between nitazoxanide and N-methylbenzimidazole were synthesized starting from the corresponding N-methyl-2-nitroanilines. The new hybrid compounds (1-13) were evaluated in vitro against Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis. NTZ, MTZ and ABZ were used as drug standards. Experimental evaluations revealed all of the new compounds (1-13) were active and showed strong activity against the three protozoa, particularly with E. histolytica where the IC50 values ranged between 3 and 69 nM.Overall, compounds 2, 5, 7, 8, 9, 11 and 12 stood out with values lower than 87 nM for all three protozoa, comparatively better than the reference drugs. (C) 2013 Elsevier Ltd. All rights reserved.