(2S,3R,4S,6R)-4-azido-6-((1,4-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)methoxy)-2-methyltetrahydro-2H-pyran-3-yl acetate | 1422391-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (2S,3R,4S,6R)-4-azido-6-((1,4-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)methoxy)-2-methyltetrahydro-2H-pyran-3-yl acetate
• CAS: 1422391-81-8
• 化学式: C₂₄H₂₃N₃O₈
• 分子量: 481.462
• InChiKey: JUENYEUOIHNDOB-DWGRVDDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  168.12
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,6R)-4-azido-6-((1,4-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)methoxy)-2-methyltetrahydro-2H-pyran-3-yl acetate 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以94%的产率得到2-((((2R,4S,5R,6S)-4-azido-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-1,4-dihydroxy-3-methylanthracene-9,10-dione
  参考文献：
  名称：

  The Structure of Anthracycline Derivatives Determines Their Subcellular Localization and Cytotoxic Activity

  摘要：

  The cytotoxic activities and subcellular localizations of clinically used and synthetic analogues of the anthracycline family of chemotherapeutic agents were studied. The structures of the anthracycline derivatives affected their cytotoxicity and the time required for these compounds to exert cytotoxic effects on tumor cells. Fluorescent DNA intercalator displacement experiments demonstrated that there was no correlation between the DNA intercalation properties and the cytotoxicity of the studied anthracycline derivatives. Confocal microscopy experiments indicated that structural differences led to differences in subcellular localization. All studied anthracycline derivatives were observed in lysosomes, suggesting that this organelle, which is involved in several processes leading to malignancy, may contain previously unidentified molecular targets for these antitumor agents.

  DOI：

  10.1021/ml3002852
• 作为产物：
  描述：

  醌茜隐色体 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.0h， 生成 (2S,3R,4S,6R)-4-azido-6-((1,4-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)methoxy)-2-methyltetrahydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  The Structure of Anthracycline Derivatives Determines Their Subcellular Localization and Cytotoxic Activity

  摘要：

  The cytotoxic activities and subcellular localizations of clinically used and synthetic analogues of the anthracycline family of chemotherapeutic agents were studied. The structures of the anthracycline derivatives affected their cytotoxicity and the time required for these compounds to exert cytotoxic effects on tumor cells. Fluorescent DNA intercalator displacement experiments demonstrated that there was no correlation between the DNA intercalation properties and the cytotoxicity of the studied anthracycline derivatives. Confocal microscopy experiments indicated that structural differences led to differences in subcellular localization. All studied anthracycline derivatives were observed in lysosomes, suggesting that this organelle, which is involved in several processes leading to malignancy, may contain previously unidentified molecular targets for these antitumor agents.

  DOI：

  10.1021/ml3002852