(-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)-phenyl]chroman-3-yl 4-(benzyloxy)benzoate | 947238-00-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)-phenyl]chroman-3-yl 4-(benzyloxy)benzoate
• CAS: 947238-00-8
• 化学式: C₆₄H₅₄O₉
• 分子量: 967.127
• InChiKey: CNOIHDANAMCIPW-VOVXCRLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.06
• 重原子数：
  73.0
• 可旋转键数：
  21.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)-phenyl]chroman-3-yl 4-(benzyloxy)benzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 4-hydroxybenzoate
  参考文献：
  名称：

  The design, synthesis and biological evaluation of pro-EGCG derivatives as novel anti-vitiligo agents

  摘要：

  一系列EGCG衍生物的前药被设计、合成，并对其在对抗H₂O₂诱导的黑色素细胞损伤中的保护效果进行了广泛评估，展示了它们在抗白癜风治疗中的潜在应用价值。

  DOI：

  10.1039/c6ra23172a
• 作为产物：
  描述：

  4-苯甲氧基苯(甲)酰氯 、 (2R,3R)-5,7-bis(benzyloxy)-2-(3,4,5-tris(benzyloxy)phenyl)chroman-3-ol 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)-phenyl]chroman-3-yl 4-(benzyloxy)benzoate
  参考文献：
  名称：

  The design, synthesis and biological evaluation of pro-EGCG derivatives as novel anti-vitiligo agents

  摘要：

  一系列EGCG衍生物的前药被设计、合成，并对其在对抗H₂O₂诱导的黑色素细胞损伤中的保护效果进行了广泛评估，展示了它们在抗白癜风治疗中的潜在应用价值。

  DOI：

  10.1039/c6ra23172a

文献信息

• Semi-synthesis and proteasome inhibition of <scp>D</scp>-ring deoxy analogs of (–)-epigallocatechin gallate (EGCG), the active ingredient of green tea extract
  作者：Congde Huo、Guoqing Shi、Wai Har Lam、Di Chen、Quizhi Cindy Cui、Q Ping Dou、Tak Hang Chan

  DOI：10.1139/v07-141

  日期：2008.6.1

  A semi-synthetic route to the D-ring analogs of (–)-epigallocatechin gallate (EGCG) from the relatively abundant (–)-epigallocatechin (EGC), isolated from green tea leaves, is described. A natural product (13), found in Cistus salvifolius, its acetate (14) and analog (17) were synthesized by this method. Their inhibitory activities against proteasomes were investigated.Key words: green tea, (–)-epigallocatechin gallate (EGCG), (–)-epigallocatechin (EGC), proteasome inhibition.

  本文描述了从绿茶叶中分离出的相对丰富的(-)-表没食子儿茶素(EGC)中获得(-)-表没食子儿茶素没食子酸酯(EGCG)D环类似物的半合成路线。用这种方法合成了肉苁蓉（Cistus salvifolius）中的一种天然产物（13）及其醋酸盐（14）和类似物（17）。关键词：绿茶；(-)-表没食子儿茶素没食子酸酯（EGCG）；(-)-表没食子儿茶素（EGC）；蛋白酶体抑制。
• Synthesis of (2R,3R)-epigallocatechin-3-O-(4-hydroxybenzoate), a novel catechin from Cistus salvifolius, and evaluation of its proteasome inhibitory activities
  作者：Kumi Osanai、Congde Huo、Kristin R. Landis-Piwowar、Q. Ping Dou、Tak Hang Chan

  DOI：10.1016/j.tet.2007.05.043

  日期：2007.8

  The total and semi syntheses of (2R, 3R)-epigallocatechin-3-O-(4-hydroxybenzoate), a novel catechin from Cistus salvifolius, were accomplished. The proteasome inhibition and cytotoxic activities of the synthetic compound and its acetyl derivative were studied and compared with (2R,3R)-epigallocatechin-3-gallate (EGCG), the active component from green tea. (C) 2007 Elsevier Ltd. All rights reserved.