2,5-dimethyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrole | 140137-35-5

• 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-(3,4,5-trimethoxyphenyl)-1H-pyrrole
• 英文别名: 2,5-Dimethyl-1-(3,4,5-trimethoxyphenyl)pyrrole
• CAS: 140137-35-5
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: XGJCYKHTLKZDQP-UHFFFAOYSA-N

物化性质

• 沸点：
  381.6±42.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrole 在 tritium oxide 作用下， 以 盐酸 为溶剂， 生成
  参考文献：
  名称：

  Jones, John R.; Hunt, Stephen; Terrier, Francois, Journal of the Chemical Society. Perkin transactions II, 1992, # 2, p. 295 - 298

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-己二酮 、 3,4,5-三甲氧基苯胺 在 silica gel 、 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 以90%的产率得到2,5-dimethyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrole
  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

文献信息

• Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials
  作者：Dinakaran Murugesan、Alka Mital、Marcel Kaiser、David M. Shackleford、Julia Morizzi、Kasiram Katneni、Michael Campbell、Alan Hudson、Susan A. Charman、Clive Yeates、Ian H. Gilbert

  DOI：10.1021/jm400009c

  日期：2013.4.11

  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.
• Jones, John R.; Hunt, Stephen; Terrier, Francois, Journal of the Chemical Society. Perkin transactions II, 1992, # 2, p. 295 - 298
  作者：Jones, John R.、Hunt, Stephen、Terrier, Francois、Buncel, Erwin

  DOI：——

  日期：——