procyanidin B2 3-O-gallate | 109280-47-9

• 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: procyanidin B2 3-O-gallate
• 英文别名: [(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 109280-47-9
• 化学式: C₃₇H₃₀O₁₆
• 分子量: 730.636
• InChiKey: BXWABJPTCUDBMM-QOCBQNCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  288
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 procyanidin B2 3-O-gallate 在 吡啶 作用下， 反应 24.0h， 以80%的产率得到3,4,5-Triacetoxy-benzoic acid (2R,3R,4R,2'R,3'R)-5,7,3',5',7'-pentaacetoxy-2,2'-bis-(3,4-diacetoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3-yl ester
  参考文献：
  名称：

  Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases

  摘要：

  Six galloyl-substituted procyanidin B1 and B2, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were systematically synthesized with the condensation method using TMSOTf as a catalyst. Their ability of DPPH radical scavenging activity and DNA polymerase inhibitory activity were also investigated. The results indicated that the galloyl group of these compounds is very important for both activities. 3,3"-Di-O-gallate dimers acted as strong inhibitor against DNA polymerase alpha and beta, whereas the desgalloyl and monogalloyl compounds did not exhibit any appreciable inhibitory activity against the DNA polymerase beta. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.023
• 作为产物：
  描述：

  [4,8’]-2,3-cis-3.4-trans:2’,3’-cis-octabenzyloxy-(-)-epicatechin-3-(tribenzyloxy)gallate 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 以78%的产率得到procyanidin B2 3-O-gallate
  参考文献：
  名称：

  Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases

  摘要：

  Six galloyl-substituted procyanidin B1 and B2, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were systematically synthesized with the condensation method using TMSOTf as a catalyst. Their ability of DPPH radical scavenging activity and DNA polymerase inhibitory activity were also investigated. The results indicated that the galloyl group of these compounds is very important for both activities. 3,3"-Di-O-gallate dimers acted as strong inhibitor against DNA polymerase alpha and beta, whereas the desgalloyl and monogalloyl compounds did not exhibit any appreciable inhibitory activity against the DNA polymerase beta. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.023

文献信息

• Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities
  作者：Manato Suda、Miyuki Katoh、Kazuya Toda、Kiriko Matsumoto、Koichiro Kawaguchi、Sei-ichi Kawahara、Yasunao Hattori、Hiroshi Fujii、Hidefumi Makabe

  DOI：10.1016/j.bmcl.2013.06.061

  日期：2013.9

  Synthesis of procyanidin B2 and B3 gallate derivatives, 3-O-gallate, 3 ''-O-gallate, and 3,3 ''-di-O-gallate, were synthesized using equimolar condensation mediated by Yb(OTf)(3). Synthesized compounds showed significant antitumor effects against human prostate PC-3 cell lines. Their activities were weaker than well-known EGCG and prodelphinidin B3. (C) 2013 Elsevier Ltd. All rights reserved.