(2S)-3-phenyl-2-[6-(3-(2-[2-(2-phenyl-1-ethynyl)-1-cyclohexenyl]-1-ethynyl)-phenyl)-5-hexynoyl]aminopropanoic acid | 303142-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-3-phenyl-2-[6-(3-(2-[2-(2-phenyl-1-ethynyl)-1-cyclohexenyl]-1-ethynyl)-phenyl)-5-hexynoyl]aminopropanoic acid
• 英文别名: (S)-3-phenyl-2-((6-(3-((2-(phenylethynyl)-1-cyclohexenyl)ethynyl)phenyl)-5-hexynoyl)amino)propanoic acid；(2S)-3-phenyl-2-[6-[3-[2-[2-(2-phenylethynyl)cyclohexen-1-yl]ethynyl]phenyl]hex-5-ynoylamino]propanoic acid
• CAS: 303142-45-2
• 化学式: C₃₇H₃₃NO₃
• 分子量: 539.674
• InChiKey: ZTWKIAZAZBJXSX-DHUJRADRSA-N

物化性质

• 沸点：
  776.1±60.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-3-phenyl-2-[6-(3-(2-[2-(2-phenyl-1-ethynyl)-1-cyclohexenyl]-1-ethynyl)-phenyl)-5-hexynoyl]aminopropanoic acid 以 异丙醇 为溶剂， 以44%的产率得到3-Phenyl-2-{6-[3-(3-phenyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl]hex-5-ynoylamino}propanoic acid
  参考文献：
  名称：

  设计烯二炔的合成及光化学活性

  摘要：

  DOI：

  10.1021/ja000766z
• 作为产物：
  描述：

  methyl(2S)-3-phenyl-2-[6-(3-(2-[2-(2-phenyl-1-ethynyl)-1-cyclohexenyl]-1-ethynyl)-phenyl)-5-hexynoyl]aminopropanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以79%的产率得到(2S)-3-phenyl-2-[6-(3-(2-[2-(2-phenyl-1-ethynyl)-1-cyclohexenyl]-1-ethynyl)-phenyl)-5-hexynoyl]aminopropanoic acid
  参考文献：
  名称：

  设计烯二炔的合成及光化学活性

  摘要：

  DOI：

  10.1021/ja000766z

文献信息

• Synthesis and Protein Degradation Capacity of Photoactivated Enediynes
  作者：Farid S. Fouad、Justin M. Wright、Gary Plourde II,、Ajay D. Purohit、Justin K. Wyatt、Ahmed El-Shafey、George Hynd、Curtis F. Crasto、Yiqing Lin、Graham B. Jones

  DOI：10.1021/jo051403q

  日期：2005.11.1

  The viability of proteins as targets of thermally and photoactivated enediynes has been confirmed at the molecular level. Model studies using a labeled substrate confirmed the efficacy of atom transfer from diyl radicals produced from enediynes to form captodatively stabilized carbon centered aminoacyl radicals, which then undergo either fragmentation or dimerization. To exploit this finding, a family of enediynes was developed using an intramolecular coupling strategy. Derivatives were prepared and used to target specific proteins, showing good correlation between affinity and photoinduced protein degrading activity. The findings have potential applications in the design of artificial chemical proteases and add to our understanding of the mechanism of action of the clinically important enediyne antitumor antibiotics.