(2R,3S,4S)-3-acetoxy-4-methoxy-5,7-3',4',5'-pentabenzyloxyflavan | 1429125-62-1

• 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,4S)-3-acetoxy-4-methoxy-5,7-3',4',5'-pentabenzyloxyflavan
• 英文别名: [(2R,3S,4S)-4-methoxy-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 1429125-62-1
• 化学式: C₅₃H₄₈O₉
• 分子量: 828.959
• InChiKey: IFWJDPSOHRQOLP-IQAVOUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  62
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

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 、 (2R,3S,4S)-3-acetoxy-4-methoxy-5,7-3',4',5'-pentabenzyloxyflavan 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以73%的产率得到[(2R,3S,4S)-4-[(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]-3-hydroxy-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-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
  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)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,3S,4S)-3-acetoxy-4-methoxy-5,7-3',4',5'-pentabenzyloxyflavan
  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 B1, B2, and B4 and their antitumor activities against human PC-3 prostate cancer cell lines
  作者：Wataru Fujii、Kazuya Toda、Kiriko Matsumoto、Koichiro Kawaguchi、Sei-ichi Kawahara、Yasunao Hattori、Hiroshi Fujii、Hidefumi Makabe

  DOI：10.1016/j.tetlet.2013.10.113

  日期：2013.12

  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.