2,5-dimethyl-1-(4-(methylthio)phenyl)-1H-pyrrole-3-carbaldehyde | 923743-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-dimethyl-1-(4-(methylthio)phenyl)-1H-pyrrole-3-carbaldehyde
• 英文别名: 2,5-dimethyl-1-[4-(methylthio)phenyl]-1H-pyrrole-3-carbaldehyde；2,5-dimethyl-1-(4-methylsulfanylphenyl)pyrrole-3-carbaldehyde
• CAS: 923743-09-3
• 化学式: C₁₄H₁₅NOS
• mdl: MFCD08444741
• 分子量: 245.345
• InChiKey: OQDUCVCWGZAWNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  47.3
• 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 、 2,5-dimethyl-1-(4-(methylthio)phenyl)-1H-pyrrole-3-carbaldehyde 在 potassium hydrogensulfate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以100%的产率得到ethyl (5E)-5-[[2,5-dimethyl-1-(4-methylsulfanylphenyl)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：

  4-氨基茴香硫醚 在 silica gel 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 3.25h， 生成 2,5-dimethyl-1-(4-(methylthio)phenyl)-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