(2S)-2-[4-[(1S,2S)-1-amino-2-methylbutyl]triazol-1-yl]-1-[4-[4-[4-[(2S)-2-[4-[(1S,2S)-1-amino-2-methylbutyl]triazol-1-yl]-3-(4-hydroxyphenyl)propanoyl]piperazin-1-yl]-6-[2-[2-[2-[[1-[3-[4-(3-piperidin-1-ium-1-ylidene-6-piperidin-1-ylxanthen-9-yl)phenyl]prop-2-ynyl]triazol-4-yl]methoxy]ethoxy]ethoxy]ethylamino]-1,3,5-triazin-2-yl]piperazin-1-yl]-3-(4-hydroxyphenyl)propan-1-one | 1401081-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S)-2-[4-[(1S,2S)-1-amino-2-methylbutyl]triazol-1-yl]-1-[4-[4-[4-[(2S)-2-[4-[(1S,2S)-1-amino-2-methylbutyl]triazol-1-yl]-3-(4-hydroxyphenyl)propanoyl]piperazin-1-yl]-6-[2-[2-[2-[[1-[3-[4-(3-piperidin-1-ium-1-ylidene-6-piperidin-1-ylxanthen-9-yl)phenyl]prop-2-ynyl]triazol-4-yl]methoxy]ethoxy]ethoxy]ethylamino]-1,3,5-triazin-2-yl]piperazin-1-yl]-3-(4-hydroxyphenyl)propan-1-one
• CAS: 1401081-45-5
• 化学式: C₈₄H₁₀₆N₂₁O₈
• 分子量: 1537.9
• InChiKey: FMULATOXVMSSRP-JWZAKHIFSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  113
• 可旋转键数：
  32
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  326
• 氢给体数：
  5
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  、 (2S)-2-[4-[(1S,2S)-1-amino-2-methylbutyl]triazol-1-yl]-1-[4-[4-[4-[(2S)-2-[4-[(1S,2S)-1-amino-2-methylbutyl]triazol-1-yl]-3-(4-hydroxyphenyl)propanoyl]piperazin-1-yl]-6-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethylamino]-1,3,5-triazin-2-yl]piperazin-1-yl]-3-(4-hydroxyphenyl)propan-1-one 在 copper(II) sulfate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (2S)-2-[4-[(1S,2S)-1-amino-2-methylbutyl]triazol-1-yl]-1-[4-[4-[4-[(2S)-2-[4-[(1S,2S)-1-amino-2-methylbutyl]triazol-1-yl]-3-(4-hydroxyphenyl)propanoyl]piperazin-1-yl]-6-[2-[2-[2-[[1-[3-[4-(3-piperidin-1-ium-1-ylidene-6-piperidin-1-ylxanthen-9-yl)phenyl]prop-2-ynyl]triazol-4-yl]methoxy]ethoxy]ethoxy]ethylamino]-1,3,5-triazin-2-yl]piperazin-1-yl]-3-(4-hydroxyphenyl)propan-1-one
  参考文献：
  名称：

  Small Molecule Ligands for Active Targeting of TrkC-Expressing Tumor Cells

  摘要：

  A small molecule motif was used in "active targeting" to deliver cytotoxic substances into tumor cells that express the TrkC receptor. Underlying this study was the hypothesis that internalization of targeted conjugates into cells would be facile if mediated by receptor binding and receptor ligand internalization. Initial experiments using 6-mercaptopurine gave encouraging data but demonstrated the importance of maintaining solubility and high cytotoxicity. Conjugates of the targeting agent with a cytotoxic rosamine (similar to a rhodamine) were more successful. Targeting of TrkC was observed, validated in a series of competition experiments featuring other TrkC ligands, and accumulation into lysosomes was observed, as expected for receptor-mediated internalization.

  DOI：

  10.1021/ml300227d