methyl 3-(2-fluorophenyl)-5-methyl-4H-1,2-oxazole-5-carboxylate | 1424394-76-2

• 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: methyl 3-(2-fluorophenyl)-5-methyl-4H-1,2-oxazole-5-carboxylate
• CAS: 1424394-76-2
• 化学式: C₁₂H₁₂FNO₃
• 分子量: 237.231
• InChiKey: DPMBSBVGEHTAAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-fluorophenyl)-5-methyl-4H-1,2-oxazole-5-carboxylate 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以41%的产率得到3-(2-fluorophenyl)-N-hydroxy-5-methyl-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
• 作为产物：
  描述：

  2-氟苯甲醛肟 在 三氯异氰尿酸 、 三乙胺 作用下， 反应 24.0h， 生成 methyl 3-(2-fluorophenyl)-5-methyl-4H-1,2-oxazole-5-carboxylate
  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

• Synthesis and evaluation of 4,5-dihydro-5-methylisoxazolin-5-carboxamide derivatives as VLA-4 antagonists
  作者：Ajay Soni、Abdul Rehman、Keshav Naik、Sunanda Dastidar、M.S. Alam、Abhijit Ray、Tridib Chaira、Vanya Shah、Venkata P. Palle、Ian A. Cliffe、Viswajanani J. Sattigeri

  DOI：10.1016/j.bmcl.2012.12.043

  日期：2013.3

  A novel set of compounds containing a 4,5-dihydro-5-methylisoxazoline have been successfully designed as VLA-4 receptor antagonists. Compound (14p) had a high receptor binding affinity of 4 nM and also found to be metabolically stable in vitro. (c) 2012 Elsevier Ltd. All rights reserved.
• 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.