benzyl 5-methyl-3-oxo-1,2-dihydropyrrole-4-carboxylate | 412282-19-0

• 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: benzyl 5-methyl-3-oxo-1,2-dihydropyrrole-4-carboxylate
• CAS: 412282-19-0
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: ZGYQLPXTOLCNRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  benzyl 5-methyl-3-oxo-1,2-dihydropyrrole-4-carboxylate 、 2,5-二甲基-1-[2-(三氟甲基)苯基]-1H-吡咯-3-甲醛 在 potassium hydrogensulfate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以95%的产率得到benzyl (5E)-5-[[2,5-dimethyl-1-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methylidene]-2-methyl-4-oxo-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials

  摘要：

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.

  DOI：

  10.1021/jm400009c
• 作为产物：
  描述：

  乙酰丙酮苄酯 在 吡啶 、 ammonium hydroxide 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， 反应 21.0h， 生成 benzyl 5-methyl-3-oxo-1,2-dihydropyrrole-4-carboxylate
  参考文献：
  名称：

  Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials

  摘要：

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.

  DOI：

  10.1021/jm400009c