gallocatechin-(4α->8)-gallocatechin-(4α->8)-catechin | 79136-97-3

• 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: gallocatechin-(4α->8)-gallocatechin-(4α->8)-catechin
• 英文别名: Prodelphinidin C2；(2R,3S,4R)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-2-(3,4,5-trihydroxyphenyl)-8-[(2R,3S,4S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 79136-97-3
• 化学式: C₄₅H₃₈O₂₀
• 分子量: 898.785
• InChiKey: RJFFPCHJOFXZQD-YTSXHMEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  65
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  372
• 氢给体数：
  17
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 gallocatechin-(4α->8)-gallocatechin-(4α->8)-catechin 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以27%的产率得到[(2R,3S)-5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-8-[(2R,3S,4R)-3,5,7-triacetyloxy-2-(3,4,5-triacetyloxyphenyl)-8-[(2R,3S,4S)-3,5,7-triacetyloxy-2-(3,4,5-triacetyloxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromen-3-yl] acetate
  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,4R)-4-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-8-yl]-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)-2-[3,4,5-tris(phenylmethoxy)phenyl]-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)-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

文献信息

• Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation
  作者：Wataru Fujii、Kazuya Toda、Koichiro Kawaguchi、Sei-ichi Kawahara、Miyuki Katoh、Yasunao Hattori、Hiroshi Fujii、Hidefumi Makabe

  DOI：10.1016/j.tet.2013.02.087

  日期：2013.4

  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.