5-chloro-2-[(methoxycarbonyl)amino]-1-methyl-1H-benzimidazole-6-carboxylic acid

• 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-chloro-2-[(methoxycarbonyl)amino]-1-methyl-1H-benzimidazole-6-carboxylic acid
• 英文别名: 6-Chloro-2-(methoxycarbonylamino)-3-methylbenzimidazole-5-carboxylic acid；6-chloro-2-(methoxycarbonylamino)-3-methylbenzimidazole-5-carboxylic acid
• 化学式: C₁₁H₁₀ClN₃O₄
• 分子量: 283.671
• InChiKey: LAQKBQIGCIBKFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-5-硝基噻唑 、 5-chloro-2-[(methoxycarbonyl)amino]-1-methyl-1H-benzimidazole-6-carboxylic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以51.11%的产率得到methyl {5-chloro-1-methyl-6-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]-1H-benzimidazol-2-yl}carbamate
  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
• 作为产物：
  描述：

  在 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 5-chloro-2-[(methoxycarbonyl)amino]-1-methyl-1H-benzimidazole-6-carboxylic acid
  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.