(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-8-[(2R,3S,4S)-3-hydroxy-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-4-yl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol | 1229517-70-7

• 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,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-8-[(2R,3S,4S)-3-hydroxy-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-4-yl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol
• CAS: 1229517-70-7
• 化学式: C₉₃H₈₀O₁₃
• 分子量: 1405.65
• InChiKey: HMPLHKMIKLJUDG-SBRYDNGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.4
• 重原子数：
  106
• 可旋转键数：
  30
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-8-[(2R,3S,4S)-3-hydroxy-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-4-yl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以96%的产率得到gallocatechin-(4α->8)-catechin
  参考文献：
  名称：

  Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation

  摘要：

  Total synthesis of prodelphinidin B3 and C2 have been accomplished. The key step is Lewis acid-mediated equimolar condensations between a catechin and/or gallocatechin nucleophile and a gallocatechin electrophile. The antitumor effects of synthetic prodelphidin B3 and C2 against PC-3 prostate cancer cell lines have been investigated. Both compounds showed significant antitumor effects. Their activity was almost the same as that of EGCG, a known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.087
• 作为产物：
  描述：

  [(2R,3S,4S)-4-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-8-yl]-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate 在 四丁基氢氧化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以82%的产率得到(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-8-[(2R,3S,4S)-3-hydroxy-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-4-yl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol
  参考文献：
  名称：

  Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation

  摘要：

  Total synthesis of prodelphinidin B3 and C2 have been accomplished. The key step is Lewis acid-mediated equimolar condensations between a catechin and/or gallocatechin nucleophile and a gallocatechin electrophile. The antitumor effects of synthetic prodelphidin B3 and C2 against PC-3 prostate cancer cell lines have been investigated. Both compounds showed significant antitumor effects. Their activity was almost the same as that of EGCG, a known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.087

文献信息

• Synthesis of Prodelphinidin Trimer Isolated from Cistus Albidus and its Growth Inhibitory Activity Against Human Prostate Cancer Cell Lines
  作者：Hidefumi Makabe、Hiroshi Fujii、Masataka Mori、Kiriko Matsumoto、Chisato Ishihara、Koichiro Kawaguchi、Sei-ichi Kawahara、Yasunao Hattori

  DOI：10.3987/com-16-13557

  日期：——

  First synthesis of prodelphinidin trimer (epigallocatechin-gallocatechin-catechin) isolated from Cistus albidus was accomplished from monomeric epigallocatechin electrophile and dimeric gallocatechin-catechin nucleophile. The condensation was worked using AgoTf as a Lewis acid and condensed product was successfully converted into titled compound in good yield. Synthesized compound showed significant growth inhibitory activity against human prostate PC-3 cell lines. Its activity was almost same as prodelphinidin B3.