tert-butyl N-[2-(3-phenylpropanoylamino)ethyl]carbamate | 1426247-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[2-(3-phenylpropanoylamino)ethyl]carbamate
• CAS: 1426247-05-3
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: FWRUSYGUNGRHSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-(3-phenylpropanoylamino)ethyl]carbamate 在 水 、 三氟乙酸 作用下， 生成 N-(3-phenylpropionyl)-1,2-ethanediamine
  参考文献：
  名称：

  Examination of the Mode of Action of the Almiramide Family of Natural Products against the Kinetoplastid Parasite Trypanosoma brucei

  摘要：

  Almiramide C is a marine natural product with low micromolar activity against Leishmania donovani, the causative agent of leishmaniasis. We have now shown that almiramide C is also active against the related parasite Ttypanosoma brucei, the causative agent of human African trypanosomiasis. A series of activity-based probes have been synthesized to explore both the molecular target of this compound series in T. brucei lysates and site localization through epifluorescence microscopy. These target identification studies indicate that the almiramides likely perturb glycosomal function through disruption of membrane assembly machinery. Glycosomes, which are organelles specific to kinetoplastid parasites, house the first seven steps of glycolysis and have been shown to be essential for parasite survival in the bloodstream stage. There are currently no reported smallmolecule disruptors of glycosome function, making the almiramides unique molecular probes for this understudied parasitespecific organelle. Additionally, examination of toxicity in an in vivo zebrafish model has shown that these compounds have little effect on organism development, even at high concentrations, and has uncovered a potential side effect through localization of fluorescent derivatives to zebrafish neuromast cells. Combined, these results further our understanding of the potential value of this lead series as development candidates against T. brucei.

  DOI：

  10.1021/np300834q
• 作为产物：
  描述：

  N-叔丁氧羰基-1,2-乙二胺 、 3-苯基丙酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以37%的产率得到tert-butyl N-[2-(3-phenylpropanoylamino)ethyl]carbamate
  参考文献：
  名称：

  Examination of the Mode of Action of the Almiramide Family of Natural Products against the Kinetoplastid Parasite Trypanosoma brucei

  摘要：

  Almiramide C is a marine natural product with low micromolar activity against Leishmania donovani, the causative agent of leishmaniasis. We have now shown that almiramide C is also active against the related parasite Ttypanosoma brucei, the causative agent of human African trypanosomiasis. A series of activity-based probes have been synthesized to explore both the molecular target of this compound series in T. brucei lysates and site localization through epifluorescence microscopy. These target identification studies indicate that the almiramides likely perturb glycosomal function through disruption of membrane assembly machinery. Glycosomes, which are organelles specific to kinetoplastid parasites, house the first seven steps of glycolysis and have been shown to be essential for parasite survival in the bloodstream stage. There are currently no reported smallmolecule disruptors of glycosome function, making the almiramides unique molecular probes for this understudied parasitespecific organelle. Additionally, examination of toxicity in an in vivo zebrafish model has shown that these compounds have little effect on organism development, even at high concentrations, and has uncovered a potential side effect through localization of fluorescent derivatives to zebrafish neuromast cells. Combined, these results further our understanding of the potential value of this lead series as development candidates against T. brucei.

  DOI：

  10.1021/np300834q

文献信息

• Examination of the Mode of Action of the Almiramide Family of Natural Products against the Kinetoplastid Parasite <i>Trypanosoma brucei</i>
  作者：Laura M. Sanchez、Giselle M. Knudsen、Claudia Helbig、Geraldine De Muylder、Samantha M. Mascuch、Zachary B. Mackey、Lena Gerwick、Christine Clayton、James H. McKerrow、Roger G. Linington

  DOI：10.1021/np300834q

  日期：2013.4.26

  Almiramide C is a marine natural product with low micromolar activity against Leishmania donovani, the causative agent of leishmaniasis. We have now shown that almiramide C is also active against the related parasite Ttypanosoma brucei, the causative agent of human African trypanosomiasis. A series of activity-based probes have been synthesized to explore both the molecular target of this compound series in T. brucei lysates and site localization through epifluorescence microscopy. These target identification studies indicate that the almiramides likely perturb glycosomal function through disruption of membrane assembly machinery. Glycosomes, which are organelles specific to kinetoplastid parasites, house the first seven steps of glycolysis and have been shown to be essential for parasite survival in the bloodstream stage. There are currently no reported smallmolecule disruptors of glycosome function, making the almiramides unique molecular probes for this understudied parasitespecific organelle. Additionally, examination of toxicity in an in vivo zebrafish model has shown that these compounds have little effect on organism development, even at high concentrations, and has uncovered a potential side effect through localization of fluorescent derivatives to zebrafish neuromast cells. Combined, these results further our understanding of the potential value of this lead series as development candidates against T. brucei.