(2R,3R)-3',4',5,7-tetra-O-benzylflavan-3-yl hexadecanoate | 909798-95-4

• 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,3R)-3',4',5,7-tetra-O-benzylflavan-3-yl hexadecanoate
• CAS: 909798-95-4
• 化学式: C₅₉H₆₈O₇
• 分子量: 889.185
• InChiKey: GUNKUHBCBGSLRV-YEHVPHQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.07
• 重原子数：
  66.0
• 可旋转键数：
  28.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3',4',5,7-tetra-O-benzylflavan-3-yl hexadecanoate 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 以66%的产率得到(2R,3R)-3',4',5,7-tetrahydroxyflavan-3-yl hexadecanoate
  参考文献：
  名称：

  Epicatechin conjugated with fatty acid is a potent inhibitor of DNA polymerase and angiogenesis

  摘要：

  Anti-cancer and anti-angiogenesis effects of green tea catechins have been demonstrated. It has been found that chemical modification of tea catechins improves their biological activities. We examined the chemical modification of epicatechin enhanced anti-cancer and anti-angiogenic effects. Epicatechin conjugated with fatty acid (acyl-catechin) strongly inhibited DNA polymerase activity, HL-60 cancer cell growth and angiogenesis. Epicatechin conjugated with palmitic acid ((2.R,3R)-3',4',5,7-tetrahydroxyflavan-3-yl hexadecanoate, epicatechin-C16) was the strongest inhibitor in DNA polymerase alpha, beta, lambda and angiogenesis assays. Epicatechin-C16 also suppressed human endothelial cell (HUVEC) tube formation on reconstituted basement membrane, suggesting that it affected not only DNA polymerase activity but also the signal transduction pathways needed for the tube formation in HUVECs. These results suggest that acylation of epicatechin is an effective chemical modification to improve the anti-cancer activity of epicatechin. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2007.01.049
• 作为产物：
  描述：

  表儿茶素 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (2R,3R)-3',4',5,7-tetra-O-benzylflavan-3-yl hexadecanoate
  参考文献：
  名称：

  Epicatechin conjugated with fatty acid is a potent inhibitor of DNA polymerase and angiogenesis

  摘要：

  Anti-cancer and anti-angiogenesis effects of green tea catechins have been demonstrated. It has been found that chemical modification of tea catechins improves their biological activities. We examined the chemical modification of epicatechin enhanced anti-cancer and anti-angiogenic effects. Epicatechin conjugated with fatty acid (acyl-catechin) strongly inhibited DNA polymerase activity, HL-60 cancer cell growth and angiogenesis. Epicatechin conjugated with palmitic acid ((2.R,3R)-3',4',5,7-tetrahydroxyflavan-3-yl hexadecanoate, epicatechin-C16) was the strongest inhibitor in DNA polymerase alpha, beta, lambda and angiogenesis assays. Epicatechin-C16 also suppressed human endothelial cell (HUVEC) tube formation on reconstituted basement membrane, suggesting that it affected not only DNA polymerase activity but also the signal transduction pathways needed for the tube formation in HUVECs. These results suggest that acylation of epicatechin is an effective chemical modification to improve the anti-cancer activity of epicatechin. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2007.01.049

文献信息

• Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives
  作者：Ki Duk Park、Sul Gi Lee、Sung Uk Kim、Sung Han Kim、Won Suck Sun、Sung Jin Cho、Do Hyeon Jeong

  DOI：10.1016/j.bmcl.2004.07.063

  日期：2004.10

  By changing the structure or replacing the gallate group of (-)-ECG, 3-O-acyl and alkyl-(-)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(-)-epicatechin derivatives (4-25) exhibited better anticancer activity than (-)-ECG and specially, compounds 6-8, 17-19, which were modified aliphatic chains with moderate sizes (C8-C12) showed strong anticancer activity (IC50 = 6.4-31.2 muM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(-)-epicatechin (18) (IC50 = 8.9, 7.9, 6.4 muM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group. (C) 2004 Elsevier Ltd. All rights reserved.