5,7,3',4'-tetra-O-benzyl-4β-(phenylsulfanyl)-catechin

• 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-4β-(phenylsulfanyl)-catechin
• 英文别名: 5,7,3',4'-tetra-O-benzyl-4β-(phenylsulphanyl)catechin；(2R,3R,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-4-phenylsulfanyl-3,4-dihydro-2H-chromen-3-ol
• 化学式: C₄₉H₄₂O₆S
• 分子量: 758.935
• InChiKey: QWPDWFRYFXXVQI-UIUHLKSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  儿茶提取物 在 三氟化硼乙醚 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 5,7,3',4'-tetra-O-benzyl-4β-(phenylsulfanyl)-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

• Procyanidin B3 synthesis: a study of leaving group and Lewis acid activator effects upon interflavan bond formation
  作者：Rima D. Alharthy、Christopher J. Hayes

  DOI：10.1016/j.tetlet.2009.12.100

  日期：2010.2

  that BF3·OEt2 was the best in terms of both yield and stereochemical control at the C4 position. This newly developed set of conditions was then used to prepare the natural product nutraceutical procyanidin B3 with complete control of stereochemistry.

  通过DDQ氧化和在（+）-儿茶素C4位置的醇捕集（丙醇，巴豆醇和炔丙醇）制备了一系列亲电醚。检查了每种醚的路易斯酸介导的C4-取代，发现炔丙基醚是最好的总体亲电子试剂。然后研究了一系列路易斯酸作为活化剂，发现在C4位置，就产率和立体化学控制而言，BF 3 ·OEt 2是最好的。然后使用这组新开发的条件在完全控制立体化学的条件下制备天然产品营养保健品原花青素B3。
• 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.