5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin | 919365-39-2

• 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: 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin
• 英文别名: [(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-8-prop-2-enyl-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 919365-39-2
• 化学式: C₇₄H₆₄O₁₀
• 分子量: 1113.32
• InChiKey: JBLLUTUKGSCVFM-CLLAMJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  84
• 可旋转键数：
  27
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到tetra-O-benzyl-3-O-(tri-O-benzylgalloyl)-8-[4'-(tetra-O-benzyl-3''-O-(tri-O-benzylgalloyl)-8''-catechinyl)-butyl]-catechin
  参考文献：
  名称：

  Synthesis and Preliminary Anticancer Activity Studies of C4 and C8-Modified Derivatives of Catechin Gallate (CG) and Epicatechin Gallate (ECG)

  摘要：

  We have developed an improved and reliable method for stereoselective functionalization at C4 of naturally occurring (+)-catechin. Our method utilizes DDQ oxidation followed by trapping of the quinonemethide intermediate with allyl alcohol. The quinonemethide intermediate can be regenerated from the allyl ether by exposure to boron trifluoride diethyl etherate. This reactive intermediate can be trapped with a wide range of external nucleophiles. NBS bromination, lithium halogen exchange, and alkylation gave access to C8-allyl derivatives of (+)-catechin, and this allyl group was used in a series of cross-metathesis experiments to prepare novel dimeric catechin-derived products. Gallate ester derivatives of the novel C4- and C8-substituted catechins were prepared, and these materials were screened for potential anticancer activity in a range of human cancer cell lines. From these preliminary cytotoxicity assays (MTT) we found that C8-propyl-catechin gallate was more active (IC50 = 31 mu M) than catechin gallate (CG, IC50 = 53 mu M) or epicatechin gallate (ECG, IC50 = 76 mu M) against the colorectal adenocarcinoma cell line HCT116. Differential sensitivity in pancreas (Pan1), bladder (RT112), stomach (MGLVA1), liver (HepG2), and fibroblasts (46Br.1G1) cell lines was also observed.

  DOI：

  10.1021/jo061740e
• 作为产物：
  描述：

  儿茶提取物 在 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 氢氟酸 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin
  参考文献：
  名称：

  Synthesis and Preliminary Anticancer Activity Studies of C4 and C8-Modified Derivatives of Catechin Gallate (CG) and Epicatechin Gallate (ECG)

  摘要：

  We have developed an improved and reliable method for stereoselective functionalization at C4 of naturally occurring (+)-catechin. Our method utilizes DDQ oxidation followed by trapping of the quinonemethide intermediate with allyl alcohol. The quinonemethide intermediate can be regenerated from the allyl ether by exposure to boron trifluoride diethyl etherate. This reactive intermediate can be trapped with a wide range of external nucleophiles. NBS bromination, lithium halogen exchange, and alkylation gave access to C8-allyl derivatives of (+)-catechin, and this allyl group was used in a series of cross-metathesis experiments to prepare novel dimeric catechin-derived products. Gallate ester derivatives of the novel C4- and C8-substituted catechins were prepared, and these materials were screened for potential anticancer activity in a range of human cancer cell lines. From these preliminary cytotoxicity assays (MTT) we found that C8-propyl-catechin gallate was more active (IC50 = 31 mu M) than catechin gallate (CG, IC50 = 53 mu M) or epicatechin gallate (ECG, IC50 = 76 mu M) against the colorectal adenocarcinoma cell line HCT116. Differential sensitivity in pancreas (Pan1), bladder (RT112), stomach (MGLVA1), liver (HepG2), and fibroblasts (46Br.1G1) cell lines was also observed.

  DOI：

  10.1021/jo061740e

文献信息

• Synthesis and Preliminary Anticancer Activity Studies of C4 and C8-Modified Derivatives of Catechin Gallate (CG) and Epicatechin Gallate (ECG)
  作者：Christopher J. Hayes、Benjamin P. Whittaker、Susan A. Watson、Anna M. Grabowska

  DOI：10.1021/jo061740e

  日期：2006.12.1

  We have developed an improved and reliable method for stereoselective functionalization at C4 of naturally occurring (+)-catechin. Our method utilizes DDQ oxidation followed by trapping of the quinonemethide intermediate with allyl alcohol. The quinonemethide intermediate can be regenerated from the allyl ether by exposure to boron trifluoride diethyl etherate. This reactive intermediate can be trapped with a wide range of external nucleophiles. NBS bromination, lithium halogen exchange, and alkylation gave access to C8-allyl derivatives of (+)-catechin, and this allyl group was used in a series of cross-metathesis experiments to prepare novel dimeric catechin-derived products. Gallate ester derivatives of the novel C4- and C8-substituted catechins were prepared, and these materials were screened for potential anticancer activity in a range of human cancer cell lines. From these preliminary cytotoxicity assays (MTT) we found that C8-propyl-catechin gallate was more active (IC50 = 31 mu M) than catechin gallate (CG, IC50 = 53 mu M) or epicatechin gallate (ECG, IC50 = 76 mu M) against the colorectal adenocarcinoma cell line HCT116. Differential sensitivity in pancreas (Pan1), bladder (RT112), stomach (MGLVA1), liver (HepG2), and fibroblasts (46Br.1G1) cell lines was also observed.