4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)ethyl)morpholine | 54609-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)ethyl)morpholine
• 英文别名: 4-[2-(2,5-Dimethylpyrrol-1-yl)ethyl]morpholine
• CAS: 54609-14-2
• 化学式: C₁₂H₂₀N₂O
• mdl: MFCD12187093
• 分子量: 208.304
• InChiKey: RGFUDGSEOFNQDE-UHFFFAOYSA-N

物化性质

• 沸点：
  172-173 °C(Press: 12 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  17.4
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)ethyl)morpholine 在 哌啶 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (2Z,5Z)-3-cyclohexyl-5-((2,5-dimethyl-1-(2-morpholinoethyl)-1H-pyrrol-3-yl)methylene)-2-(phenylimino)thiazolidin-4-one
  参考文献：
  名称：

  Discovery and optimisation studies of antimalarial phenotypic hits

  摘要：

  There is an urgent need for the development of new antimalarial compounds. As a result of a phenotypic screen, several compounds with potent activity against the parasite Plasmodium falciparum were identified. Characterization of these compounds is discussed, along with approaches to optimise the physicochemical properties. The in vitro antimalarial activity of these compounds against P. falciparum K1 had EC50 values in the range of 0.09-29 mu M, and generally good selectivity (typically >100-fold) compared to a mammalian cell line (L6). One example showed no significant activity against a rodent model of malaria, and more work is needed to optimise these compounds. (C) 2015 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.08.044
• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 在 苯 作用下， 生成 4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)ethyl)morpholine
  参考文献：
  名称：

  New 2,5-Dimethylpyrrole Derivatives

  摘要：

  DOI：

  10.1021/ja01228a502

文献信息

• FURTHER STUDIES ON THE KNORR-PAAL SYNTHESIS OF 2,5-DIALKYLPYRROLES
  作者：NG. PH. BUU-HOÏ、NG. D. XUONG

  DOI：10.1021/jo01125a008

  日期：1955.7
• 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.
• New 2,5-Dimethylpyrrole Derivatives
  作者：W. S. Bishop

  DOI：10.1021/ja01228a502

  日期：1945.12
• Discovery and optimisation studies of antimalarial phenotypic hits
  作者：Alka Mital、Dinakaran Murugesan、Marcel Kaiser、Clive Yeates、Ian H. Gilbert

  DOI：10.1016/j.ejmech.2015.08.044

  日期：2015.10

  There is an urgent need for the development of new antimalarial compounds. As a result of a phenotypic screen, several compounds with potent activity against the parasite Plasmodium falciparum were identified. Characterization of these compounds is discussed, along with approaches to optimise the physicochemical properties. The in vitro antimalarial activity of these compounds against P. falciparum K1 had EC50 values in the range of 0.09-29 mu M, and generally good selectivity (typically >100-fold) compared to a mammalian cell line (L6). One example showed no significant activity against a rodent model of malaria, and more work is needed to optimise these compounds. (C) 2015 The Authors. Published by Elsevier Masson SAS.