3-methyldigiferrol | 69414-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-methyldigiferrol
• 英文别名: 1,4-Dihydroxy-2-hydroxymethyl-3-methylanthraquinone；1,4-dihydroxy-2-(hydroxymethyl)-3-methylanthracene-9,10-dione
• CAS: 69414-61-5
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: LNIPMARXYXMVKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyldigiferrol 在 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 2-[[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxymethyl]-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：

  聚合甲醛 、 醌茜隐色体 、 sodium methylate 在 氧气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-methyldigiferrol
  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

文献信息

• KROHN K.; HEMME C., LIEBIGS ANN. CHEM., 1979, NO 1, 19-34
  作者：KROHN K.、 HEMME C.

  DOI：——

  日期：——