5,7-di-O-tritylsilybin | 944443-36-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: 5,7-di-O-tritylsilybin
• 英文别名: (2R,3R)-3-hydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-5,7-ditrityloxy-2,3-dihydrochromen-4-one
• CAS: 944443-36-1
• 化学式: C₆₃H₅₀O₁₀
• 分子量: 967.084
• InChiKey: BFJJPTPSKARUPE-CJJAXIKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  73
• 可旋转键数：
  14
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,7-di-O-tritylsilybin 、 3,4,5-三苄氧基苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters

  摘要：

  The synthesis of various silybin monogalloyl esters was developed, and their antiangiogenic activities were evaluated in a variety of in vitro tests with human umbilical vein endothelial cells (HUVECs). A structure activity relationship (SAR) study found the regioselectivity of the silybin galloylation to be highly significant. Silybin (as an equimolar mixture of two diastereomers A and B) exhibited quite poor antiangiogenic activities, whereas its El stereoisomer is more active than silybin A. The galloylation of phenolic OH groups of natural silybin (a mixture of both isomers) leads to increases in their antiangiogenic activities, which is more apparent with the 7-OH than the 20-OH. In contrast, gallates at aliphatic OH groups either had a comparable activity to the parent compound or are even worse than silybin, which was observed in the case of 3-O-galloylsilybin. The most effective compound from this series (7-O-galloylsilybin) has also been prepared from stereochemically pure silybins A and B to evaluate the effect of stereochemistry on the activity. As with silybin itself, the B isomer of 7-O-galloylsilybin was more active than A isomer.

  DOI：

  10.1021/jm201034h
• 作为产物：
  描述：

  水飞蓟素A,B 、 三苯基氯甲烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 5,7-di-O-tritylsilybin
  参考文献：
  名称：

  Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters

  摘要：

  The synthesis of various silybin monogalloyl esters was developed, and their antiangiogenic activities were evaluated in a variety of in vitro tests with human umbilical vein endothelial cells (HUVECs). A structure activity relationship (SAR) study found the regioselectivity of the silybin galloylation to be highly significant. Silybin (as an equimolar mixture of two diastereomers A and B) exhibited quite poor antiangiogenic activities, whereas its El stereoisomer is more active than silybin A. The galloylation of phenolic OH groups of natural silybin (a mixture of both isomers) leads to increases in their antiangiogenic activities, which is more apparent with the 7-OH than the 20-OH. In contrast, gallates at aliphatic OH groups either had a comparable activity to the parent compound or are even worse than silybin, which was observed in the case of 3-O-galloylsilybin. The most effective compound from this series (7-O-galloylsilybin) has also been prepared from stereochemically pure silybins A and B to evaluate the effect of stereochemistry on the activity. As with silybin itself, the B isomer of 7-O-galloylsilybin was more active than A isomer.

  DOI：

  10.1021/jm201034h

文献信息

• Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters
  作者：Radek Gažák、Kateřina Valentová、Kateřina Fuksová、Petr Marhol、Marek Kuzma、Miguel Ángel Medina、Ivana Oborná、Jitka Ulrichová、Vladimír Křen

  DOI：10.1021/jm201034h

  日期：2011.10.27

  The synthesis of various silybin monogalloyl esters was developed, and their antiangiogenic activities were evaluated in a variety of in vitro tests with human umbilical vein endothelial cells (HUVECs). A structure activity relationship (SAR) study found the regioselectivity of the silybin galloylation to be highly significant. Silybin (as an equimolar mixture of two diastereomers A and B) exhibited quite poor antiangiogenic activities, whereas its El stereoisomer is more active than silybin A. The galloylation of phenolic OH groups of natural silybin (a mixture of both isomers) leads to increases in their antiangiogenic activities, which is more apparent with the 7-OH than the 20-OH. In contrast, gallates at aliphatic OH groups either had a comparable activity to the parent compound or are even worse than silybin, which was observed in the case of 3-O-galloylsilybin. The most effective compound from this series (7-O-galloylsilybin) has also been prepared from stereochemically pure silybins A and B to evaluate the effect of stereochemistry on the activity. As with silybin itself, the B isomer of 7-O-galloylsilybin was more active than A isomer.