3-((((2R,4R,5R,6S)-4-azido-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-1,8-dihydroxyanthracene-9,10-dione | 1309862-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-((((2R,4R,5R,6S)-4-azido-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-1,8-dihydroxyanthracene-9,10-dione
• CAS: 1309862-19-8
• 化学式: C₂₁H₁₉N₃O₇
• 分子量: 425.398
• InChiKey: QGYYMAOEGBECLE-UGDBAASPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  162.05
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-((((2R,4R,5R,6S)-4-azido-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-1,8-dihydroxyanthracene-9,10-dione 在 palladium on carbon 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 以93%的产率得到3-[[(2R,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxymethyl]-1,8-dihydroxyanthracene-9,10-dione
  参考文献：
  名称：

  Targeting Anthracycline-Resistant Tumor Cells with Synthetic Aloe-Emodin Glycosides

  摘要：

  The cytotoxic activity of aloe-emodin (AE), a natural anthranoid that readily permeates anthracycline-resistant tumor cells, was improved by the attachment of an amino-sugar unit to its anthraquinone core. The new class of AE glycosides (AEGs) showed a significant improvement in cytotoxicity-up to more than 2 orders of magnitude greater than those of AE and the clinically used anthracycline doxorubicin (DOX)-against several cancer cell lines with different levels of DOX resistance. Incubation with the synthetic AEGs induced cell death in less than one cell cycle, indicating that these compounds do not directly target the cell division mechanism. Confocal microscopy provided evidence that unlike DOX, AEGs accumulated in anthracycline-resistant tumor cells in which resistance is conferred by P-glycoprotein efflux pumps. The results of this study demonstrate that AEGs may serve as a promising scaffold for the development of cytotoxic agents capable of overcoming anthracycline resistance in tumor cells.

  DOI：

  10.1021/ml2001104
• 作为产物：
  描述：

  (2S,3R,4R,6R)-4-azido-6-((4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methoxy)-2-methyltetrahydro-2H-pyran-3-yl acetate 在 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以95%的产率得到3-((((2R,4R,5R,6S)-4-azido-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-1,8-dihydroxyanthracene-9,10-dione
  参考文献：
  名称：

  Targeting Anthracycline-Resistant Tumor Cells with Synthetic Aloe-Emodin Glycosides

  摘要：

  The cytotoxic activity of aloe-emodin (AE), a natural anthranoid that readily permeates anthracycline-resistant tumor cells, was improved by the attachment of an amino-sugar unit to its anthraquinone core. The new class of AE glycosides (AEGs) showed a significant improvement in cytotoxicity-up to more than 2 orders of magnitude greater than those of AE and the clinically used anthracycline doxorubicin (DOX)-against several cancer cell lines with different levels of DOX resistance. Incubation with the synthetic AEGs induced cell death in less than one cell cycle, indicating that these compounds do not directly target the cell division mechanism. Confocal microscopy provided evidence that unlike DOX, AEGs accumulated in anthracycline-resistant tumor cells in which resistance is conferred by P-glycoprotein efflux pumps. The results of this study demonstrate that AEGs may serve as a promising scaffold for the development of cytotoxic agents capable of overcoming anthracycline resistance in tumor cells.

  DOI：

  10.1021/ml2001104

文献信息

• [EN] ALOE-EMODIN DERIVATIVES AND USE THEREOF FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS D'ALOÉ-ÉMODINE ET LEUR UTILISATION POUR LE TRAITEMENT DU CANCER
  申请人：UNIV RAMOT

  公开号：WO2011089602A3

  公开（公告）日：2011-12-29