1-N-(4-羟基苯甲酰基)-1,4-二氨基丁烷 | 857263-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-N-(4-羟基苯甲酰基)-1,4-二氨基丁烷
• 英文名称: 1-N-(4-hydroxybenzoyl)-1,4-diaminobutane
• 英文别名: N-(4-aminobutyl)-4-hydroxybenzamide
• CAS: 857263-11-7
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: PDGYECHGNBAHIS-UHFFFAOYSA-N

物化性质

• 沸点：
  442.1±30.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[4-[[3-[4-(3-Aminopropylamino)butylamino]propylamino]methyl]phenoxy]anthracene-1,4-dione;2,2,2-trifluoroacetic acid 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 1-N-(4-羟基苯甲酰基)-1,4-二氨基丁烷
  参考文献：
  名称：

  Conjugation of Quinones with Natural Polyamines: Toward an Expanded Antitrypanosomatid Profile

  摘要：

  A combinatorial library of quinone-polyamine conjugates designed to optimize the antitrypanosomatid profile of hit compounds 1 and 2 has been prepared by a solid-phase approach. The conjugates were evaluated against the three most important human trypanosomatid pathogens (Trypanosoma brucei rhodesiense, Trypanosoma cruzi, and Leishmania donovani), and several showed promising activity. A subset also inhibited trypanothione reductase in vitro and induced oxidase activity of the enzyme. A highly potent analogue (7) was identified with activity against T. brucei as low as 70 nM and a selectivity index of 72. Interestingly, the presence of a cadaverine tail confers to 7 the ability to target mitochondrial function in Leishmania. In fact, in L. donovani promastigotes, we verified for 7 a decrease of cytoplasmic ATP and mitochondrial potential. Therefore, the current results support the suitability of the conjugation approach for the development of novel polyamine conjugates with enhanced therapeutic potential.

  DOI：

  10.1021/jm301112z

文献信息

• 1,3-Dimethyllumazine Derivatives from <i>Limnatis </i><i>n</i><i>ilotica</i>
  作者：Gerard Voerman、Silvia Cavalli、Gijsbert A. van der Marel、Wolfgang Pfleiderer、Jacques H. van Boom、Dmitri V. Filippov

  DOI：10.1021/np049617a

  日期：2005.6.1

  Two previously unknown lumazine derivatives, 1 and 2, have been isolated from the parasitic freshwater leech Limnatis nilotica. The structures of the compounds have been elucidated by NMR and unambiguously corroborated by chemical synthesis.
• Conjugation of Quinones with Natural Polyamines: Toward an Expanded Antitrypanosomatid Profile
  作者：Federica Lizzi、Giacomo Veronesi、Federica Belluti、Christian Bergamini、Almudena López-Sánchez、Marcel Kaiser、Reto Brun、R. Luise Krauth-Siegel、Dennis G. Hall、Luis Rivas、Maria Laura Bolognesi

  DOI：10.1021/jm301112z

  日期：2012.12.13

  A combinatorial library of quinone-polyamine conjugates designed to optimize the antitrypanosomatid profile of hit compounds 1 and 2 has been prepared by a solid-phase approach. The conjugates were evaluated against the three most important human trypanosomatid pathogens (Trypanosoma brucei rhodesiense, Trypanosoma cruzi, and Leishmania donovani), and several showed promising activity. A subset also inhibited trypanothione reductase in vitro and induced oxidase activity of the enzyme. A highly potent analogue (7) was identified with activity against T. brucei as low as 70 nM and a selectivity index of 72. Interestingly, the presence of a cadaverine tail confers to 7 the ability to target mitochondrial function in Leishmania. In fact, in L. donovani promastigotes, we verified for 7 a decrease of cytoplasmic ATP and mitochondrial potential. Therefore, the current results support the suitability of the conjugation approach for the development of novel polyamine conjugates with enhanced therapeutic potential.