(2R,3S,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate | 828249-32-7

• 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,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate
• 英文别名: [(2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-4-(2-ethoxyethoxy)-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 828249-32-7
• 化学式: C₇₅H₆₈O₁₂
• 分子量: 1161.36
• InChiKey: YKBRJJPUOZIIHF-YXISRYAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15
• 重原子数：
  87
• 可旋转键数：
  30
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,3S)-5,7-二(苄氧基)-2-[3,4-二(苄氧基)苯基]-3-色满醇 、 (2R,3S,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以71%的产率得到[4,8’]-2,3-trans-3.4-trans:2’,3’-trans-octabenzyloxy-(+)-catechin-3-(tribenzyloxy)gall
  参考文献：
  名称：

  Stereoselective synthesis of procyanidin B3-3-O-gallate and 3,3″-di-O-gallate, and their abilities as antioxidant and DNA polymerase inhibitor

  摘要：

  A simple method for the synthesis of procyanidin B3 substituted with a galloyl group at the 3 and 3" position is described. Condensation of a benzylated catechin-3-O-gallate electrophile with a nucleophile, catechin and catechin-3-O-gallate, proceeded smoothly and stereoselectively to afford the corresponding dimer gallates, procyanidin B3-3-O-gallate and procyanidin B3-3,3"-di-O-gallate, in good yields. Further, their antioxidant activities on UV-induced lipid peroxide formation, DPPH radical scavenging activity and inhibitory activity of DNA polymerase were also investigated. Among three procyanidin B3 congeners (procyanidin B3, 3-O-gallate and 3,3"-di-O-gallate), the 3,3"-di-O-gallate derivative showed the strongest antioxidant and radical scavenging activity. Interestingly, the 3-O-gallate derivative was the strongest inhibitor of mammalian DNA polymerase a with IC50 value of 0.26 muM, although it showed the weakest antioxidant and radical scavenging activity. It became apparent that the presence of a galloyl group at the C-3 position in the proanthocyanidin oligomer was very important for biological activity, however, the antioxidant activity of these compounds was not parallel to the DNA polymerase inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.048
• 作为产物：
  描述：

  3,4,5-三苄氧基苯甲酸 、 5,7,3′,4′-tetra-O-benzyl-4β-(2-ethoxyethoxy)-(+)-catechin 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以56%的产率得到(2R,3S,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate
  参考文献：
  名称：

  Stereoselective synthesis of procyanidin B3-3-O-gallate and 3,3″-di-O-gallate, and their abilities as antioxidant and DNA polymerase inhibitor

  摘要：

  A simple method for the synthesis of procyanidin B3 substituted with a galloyl group at the 3 and 3" position is described. Condensation of a benzylated catechin-3-O-gallate electrophile with a nucleophile, catechin and catechin-3-O-gallate, proceeded smoothly and stereoselectively to afford the corresponding dimer gallates, procyanidin B3-3-O-gallate and procyanidin B3-3,3"-di-O-gallate, in good yields. Further, their antioxidant activities on UV-induced lipid peroxide formation, DPPH radical scavenging activity and inhibitory activity of DNA polymerase were also investigated. Among three procyanidin B3 congeners (procyanidin B3, 3-O-gallate and 3,3"-di-O-gallate), the 3,3"-di-O-gallate derivative showed the strongest antioxidant and radical scavenging activity. Interestingly, the 3-O-gallate derivative was the strongest inhibitor of mammalian DNA polymerase a with IC50 value of 0.26 muM, although it showed the weakest antioxidant and radical scavenging activity. It became apparent that the presence of a galloyl group at the C-3 position in the proanthocyanidin oligomer was very important for biological activity, however, the antioxidant activity of these compounds was not parallel to the DNA polymerase inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.048

文献信息

• Synthesis of Galloyl-substituted Procyanidin B4 Series, and Their DPPH Radical Scavenging Activity and DNA Polymerase Inhibitory Activity
  作者：Noriyuki Nakajima、Hironori Sakuda、Akiko Saito、Yoshiyuki Mizushina、Hiromi Yoshida、Akira Tanaka

  DOI：10.3987/com-05-s(t)11

  日期：——
• Stereoselective synthesis of procyanidin B3-3-O-gallate and 3,3″-di-O-gallate, and their abilities as antioxidant and DNA polymerase inhibitor
  作者：Akiko Saito、Mana Emoto、Akira Tanaka、Yuki Doi、Kazuaki Shoji、Yoshiyuki Mizushina、Hiroshi Ikawa、Hiromi Yoshida、Nobuyasu Matsuura、Noriyuki Nakajima

  DOI：10.1016/j.tet.2004.10.048

  日期：2004.12

  A simple method for the synthesis of procyanidin B3 substituted with a galloyl group at the 3 and 3" position is described. Condensation of a benzylated catechin-3-O-gallate electrophile with a nucleophile, catechin and catechin-3-O-gallate, proceeded smoothly and stereoselectively to afford the corresponding dimer gallates, procyanidin B3-3-O-gallate and procyanidin B3-3,3"-di-O-gallate, in good yields. Further, their antioxidant activities on UV-induced lipid peroxide formation, DPPH radical scavenging activity and inhibitory activity of DNA polymerase were also investigated. Among three procyanidin B3 congeners (procyanidin B3, 3-O-gallate and 3,3"-di-O-gallate), the 3,3"-di-O-gallate derivative showed the strongest antioxidant and radical scavenging activity. Interestingly, the 3-O-gallate derivative was the strongest inhibitor of mammalian DNA polymerase a with IC50 value of 0.26 muM, although it showed the weakest antioxidant and radical scavenging activity. It became apparent that the presence of a galloyl group at the C-3 position in the proanthocyanidin oligomer was very important for biological activity, however, the antioxidant activity of these compounds was not parallel to the DNA polymerase inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.