1-[4-(dimethylaminomethyl)phenyl]-2,5-dimethyl-1H-pyrrole-3-carbaldehyde | 1428183-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-[4-(dimethylaminomethyl)phenyl]-2,5-dimethyl-1H-pyrrole-3-carbaldehyde
• 英文别名: 1-[4-[(Dimethylamino)methyl]phenyl]-2,5-dimethylpyrrole-3-carbaldehyde；1-[4-[(dimethylamino)methyl]phenyl]-2,5-dimethylpyrrole-3-carbaldehyde
• CAS: 1428183-44-1
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: KZWHJJNAUZCUPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 5-methyl-3-oxo-1,2-dihydropyrrole-4-carboxylate 、 1-[4-(dimethylaminomethyl)phenyl]-2,5-dimethyl-1H-pyrrole-3-carbaldehyde 在 potassium hydrogensulfate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到ethyl (5E)-5-[[1-[4-[(dimethylamino)methyl]phenyl]-2,5-dimethylpyrrol-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：

  N,N-二甲基-4-硝基苄胺 在 palladium 10% on activated carbon 、 氢气 、 silica gel 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.25h， 生成 1-[4-(dimethylaminomethyl)phenyl]-2,5-dimethyl-1H-pyrrole-3-carbaldehyde
  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