[4,8’]-2,3-trans-3.4-trans:2’,3’-cis-decabenzyloxy-(+)-gallocatechin-(-)-epigallocatechin | 1499167-15-5

• 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: [4,8’]-2,3-trans-3.4-trans:2’,3’-cis-decabenzyloxy-(+)-gallocatechin-(-)-epigallocatechin
• CAS: 1499167-15-5
• 化学式: C₁₀₀H₈₆O₁₄
• 分子量: 1511.77
• InChiKey: ZWPVKVRSNKHZHB-DEHAYNRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.14
• 重原子数：
  114.0
• 可旋转键数：
  33.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  151.22
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  [4,8’]-2,3-trans-3.4-trans:2’,3’-cis-decabenzyloxy-(+)-gallocatechin-(-)-epigallocatechin 在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以100%的产率得到(+)-gallocatechin-(4α->8')-epigallocatechin
  参考文献：
  名称：

  Syntheses of prodelphinidin B1, B2, and B4 and their antitumor activities against human PC-3 prostate cancer cell lines

  摘要：

  Total synthesis of prodelphinidin B1, B2, and B4 has been accomplished. The key step is Lewis acid-mediated equimolar condensations between an epigallocatechin and/or a gallocatechin nucleophile and an epigallocatechin and/or a gallocatechin electrophile. The antitumor effects of synthetic prodelphinidin B1-B4 against human PC-3 prostate cancer cell lines have been investigated. These compounds showed significant antitumor effects. Their activity seemed to be little bit stronger than EGCG and prodelphinidin B3, known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.113
• 作为产物：
  描述：

  [4,8’]-2,3-trans-3.4-trans:2’,3’-cis-3-acetoxydecabenzyloxy-(+)-gallocatechin-(-)-epigallocatechin 在 四丁基氢氧化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 68.0h， 以79%的产率得到[4,8’]-2,3-trans-3.4-trans:2’,3’-cis-decabenzyloxy-(+)-gallocatechin-(-)-epigallocatechin
  参考文献：
  名称：

  Syntheses of prodelphinidin B1, B2, and B4 and their antitumor activities against human PC-3 prostate cancer cell lines

  摘要：

  Total synthesis of prodelphinidin B1, B2, and B4 has been accomplished. The key step is Lewis acid-mediated equimolar condensations between an epigallocatechin and/or a gallocatechin nucleophile and an epigallocatechin and/or a gallocatechin electrophile. The antitumor effects of synthetic prodelphinidin B1-B4 against human PC-3 prostate cancer cell lines have been investigated. These compounds showed significant antitumor effects. Their activity seemed to be little bit stronger than EGCG and prodelphinidin B3, known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.113