Benzoic acid, 4-amino-2-chloro-5-(methylamino)-, methyl ester | 1446718-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid, 4-amino-2-chloro-5-(methylamino)-, methyl ester
• 英文别名: methyl 4-amino-2-chloro-5-(methylamino)benzoate
• CAS: 1446718-10-0
• 化学式: C₉H₁₁ClN₂O₂
• 分子量: 214.652
• InChiKey: QCLWUZIUYRSDAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzoic acid, 4-amino-2-chloro-5-(methylamino)-, methyl ester 在 盐酸 、 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 5-chloro-1-methyl-2-(trifluoromethyl)-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
• 作为产物：
  描述：

  在 氢气 作用下， 以 甲醇 为溶剂， 生成 Benzoic acid, 4-amino-2-chloro-5-(methylamino)-, methyl ester
  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 novel 2-{[2-(1H-imidazol-1-yl)ethyl]sulfanyl}-1H-benzimidazole derivatives
  作者：Jaime Pérez-Villanueva、Alicia Hernández-Campos、Lilián Yépez-Mulia、Carlos Méndez-Cuesta、Oscar Méndez-Lucio、Francisco Hernández-Luis、Rafael Castillo

  DOI：10.1016/j.bmcl.2013.05.012

  日期：2013.7

  A series of 19 new 2-[2-(1H-imidazol-1-yl)ethyl]sulfanyl}-1H-benzimidazole derivatives was synthesized starting from the properly substituted 1,2-phenylendiamine. These compounds have hydrogen or methyl at position 1; while hydrogen, chlorine, ethoxy or methoxycarbonyl group is at position 5 and/or 6. The novel compounds were tested against protozoa Trichomonas vaginalis, Giardia intestinalis and

  从适当取代的1,2-苯二胺开始，合成了一系列19种新的2-[2-（1（H-咪唑-1-基）乙基]硫烷基} -1 H-苯并咪唑衍生物。这些化合物在位置1处有氢或甲基。而氢，氯，乙氧基或甲氧羰基位于5和/或6位。测试了该新型化合物的抗原生动物阴道毛滴虫，肠道贾第鞭毛虫和溶组织变形虫。实验评估表明，所有被测化合物具有很强的活性，其IC 50值在纳摩尔范围内，甚至优于甲硝唑，它们是这些寄生虫的首选药物。