3-(2-chlorophenyl)-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide | 1513848-01-5

• 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: 3-(2-chlorophenyl)-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide
• 英文别名: 3-(2-chlorophenyl)-N-hydroxy-4,5-dihydro-1,2-oxazole-5-carboxamide
• CAS: 1513848-01-5
• 化学式: C₁₀H₉ClN₂O₃
• 分子量: 240.646
• InChiKey: HPORMOUZMGGMJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻氯苯甲醛肟 在 三氯异氰尿酸 、 盐酸羟胺 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 3-(2-chlorophenyl)-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Hydroxamic Acid Derivatives as Promising Agents for the Management of Chagas Disease

  摘要：

  Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5 ''. -dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g)was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to <1 mu M). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.

  DOI：

  10.1021/jm400902y

文献信息

• Design, Synthesis, and Evaluation of Hydroxamic Acid Derivatives as Promising Agents for the Management of Chagas Disease
  作者：Giseli Capaci Rodrigues、Daniel Ferreira Feijó、Marcelo Torres Bozza、Peiwen Pan、Daniela Vullo、Seppo Parkkila、Claudiu T. Supuran、Clemente Capasso、Alcino Palermo Aguiar、Alane Beatriz Vermelho

  DOI：10.1021/jm400902y

  日期：2014.1.23

  Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5 ''. -dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g)was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to <1 mu M). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.