5-methoxy-6-hydroxy-7-O-β-rutinosyl-2-methylchromone | 1274775-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxy-6-hydroxy-7-O-β-rutinosyl-2-methylchromone
• 英文别名: 6-hydroxy-5-methoxy-2-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CAS: 1274775-75-5
• 化学式: C₂₃H₃₀O₁₄
• 分子量: 530.483
• InChiKey: YQMNJOQRGDZDKY-JVBHFNPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  齿阿米素 在 三乙烯二胺 、 4-二甲氨基吡啶 、 potassium dichromate 、 硫酸 、 四丁基溴化铵 、 sodium methylate 、 氯化铋 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 132.0h， 生成 5-methoxy-6-hydroxy-7-O-β-rutinosyl-2-methylchromone
  参考文献：
  名称：

  Concise Synthesis of 5-Methoxy-6-hydroxy-2-methylchromone-7-O- and 5-Hydroxy-2-methylchromone-7-O-rutinosides. Investigation of Their Cytotoxic Activities against Several Human Tumor Cell Lines

  摘要：

  The synthesis of two novel 2-methylchromone-7-O-rutinosides is reported, and the in vitro biological activities of these compounds and their synthetic precursors have been investigated on the basis of their cytotoxicity against several human tumor cell lines. The synthesis features early stage assembly of the acidic labile glycosidic bond between sugar and 2-methylchromone aglycon under phase transfer catalyzed glycosidation conditions, whereas all the other standard glycosylation conditions specific to a wide array of rutinosyl donors bearing different anomeric leaving groups (e.g., SPh, OC(NH)CCl3, Br, OH groups) failed to furnish any detectable products.

  DOI：

  10.1021/jo102325s

文献信息

• Concise Synthesis of 5-Methoxy-6-hydroxy-2-methylchromone-7-<i>O</i>- and 5-Hydroxy-2-methylchromone-7-<i>O</i>-rutinosides. Investigation of Their Cytotoxic Activities against Several Human Tumor Cell Lines
  作者：Baolin Wu、Wenpeng Zhang、Zhonghua Li、Li Gu、Xin Wang、Peng George Wang

  DOI：10.1021/jo102325s

  日期：2011.4.1

  The synthesis of two novel 2-methylchromone-7-O-rutinosides is reported, and the in vitro biological activities of these compounds and their synthetic precursors have been investigated on the basis of their cytotoxicity against several human tumor cell lines. The synthesis features early stage assembly of the acidic labile glycosidic bond between sugar and 2-methylchromone aglycon under phase transfer catalyzed glycosidation conditions, whereas all the other standard glycosylation conditions specific to a wide array of rutinosyl donors bearing different anomeric leaving groups (e.g., SPh, OC(NH)CCl3, Br, OH groups) failed to furnish any detectable products.