Epicatechin 3-O-p-hydroxybenzoate | 108907-45-5

• 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: Epicatechin 3-O-p-hydroxybenzoate
• 英文别名: [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 4-hydroxybenzoate
• CAS: 108907-45-5
• 化学式: C₂₂H₁₈O₈
• 分子量: 410.4
• InChiKey: HRNWMQFQEGGZKA-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Epicatechin 3-O-p-hydroxybenzoate 以 氯仿 为溶剂， 生成 (-)-(2R,3R)-5,7-dihydroxy-2-(3,4-dihydroxyphenyl)chroman-3-yl 4-hydroxybenzoate pentaacetate
  参考文献：
  名称：

  (-)-EPIGALLOCATECHIN GALLATE DERIVATIVES FOR INHIBITING PROTEASOME

  摘要：

  一种减少肿瘤细胞生长的方法，该方法包括给予一种具有以下公式的化合物的有效量：

  公开号：

  US20160068503A1

文献信息

• (-)-Epigallocatechin Gallate Derivatives For Inhibiting Proteasome
  申请人：Chan Tak-Hang

  公开号：US20080176931A1

  公开（公告）日：2008-07-24

  (−)-EGCG, the most abundant catechin, was found to be chemopreventive and anticancer agent. However, (−)-EGCG has at least one limitation: it gives poor bioavailability. This invention provides compounds of generally formulae below, wherein R 11 , R 12 , R 13 , R 21 , R 22 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of —H, and C 1 to C 10 acyloxyl group; and R 5 is selected from the group consisting of —H, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 7 -cycloalkyl, phenyl, benzyl and C 3 -C 7 -cycloalkenyl, whereas each of the last mentioned 7 groups can be substituted with any combination of one to six halogen atoms; at least one of R 11 , R 12 , R 13 , R 21 , R 22 , R 2 , R 3 and R 4 is —H, which were found to be more potent than their non-protected counterparts, which can be used as proteasome inhibitors to reduce tumor cell growth.

  (-)-EGCG是最丰富的儿茶素之一，被发现具有化学预防和抗癌作用。然而，(-)-EGCG至少存在一个限制：其生物利用度较低。本发明提供了一般化学式如下的化合物，其中R11、R12、R13、R21、R22、R2、R3和R4各自独立地选择自-H和C1到C10酰氧基的群组成；而R5选择自-H、C1-C10烷基、C2-C10烯基、C2-C10炔基、C3-C7环烷基、苯基、苄基和C3-C7环烯基，而最后提到的7个基团中的每一个都可以用任意组合的1到6个卤素原子取代；其中至少有一个是R11、R12、R13、R21、R22、R2、R3和R4中的-H，这些化合物比其非保护的对应物更有效，可用作蛋白酶体抑制剂来减少肿瘤细胞生长。
• (−)-epigallocatechin gallate derivatives for inhibiting proteasome
  申请人：The Hong Kong Polytechnic University

  公开号：US08193377B2

  公开（公告）日：2012-06-05

  (−)-EGCG, the most abundant catechin, was found to be chemopreventive and anticancer agent. However, (−)-EGCG has at least one limitation: it gives poor bioavailability. This invention provides compounds of generally formulae below, wherein R11, R12, R13, R21, R22, R2, R3, and R4 are each independently selected from the group consisting of —H, and C1 to C10 acyloxyl group; and R5 is selected from the group consisting of —H, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C7-cycloalkyl, phenyl, benzyl and C3-C7-cycloalkenyl, whereas each of the last mentioned 7 groups can be substituted with any combination of one to six halogen atoms; at least one of R11, R12, R13, R21, R22, R2, R3 and R4 is —H, which were found to be more potent than their non-protected counterparts, which can be used as proteasome inhibitors to reduce tumor cell growth.

  (-)-EGCG是最丰富的儿茶素之一，具有化学预防和抗癌作用。然而，(-)-EGCG至少存在一个限制：其生物利用度较低。本发明提供了通式如下的化合物，其中R11、R12、R13、R21、R22、R2、R3和R4各自独立地选自由—H和C1到C10的酰氧基团组成的群体；而R5选自由—H、C1-C10-烷基、C2-C10-烯基、C2-C10-炔基、C3-C7-环烷基、苯基、苄基和C3-C7-环烯基组成的群体，其中最后提到的7个基团中的每一个都可以用任意组合的1到6个卤素原子替代；R11、R12、R13、R21、R22、R2、R3和R4中至少有一个为—H，这些化合物比其非保护的对应物更有效，可用作蛋白酶体抑制剂来减少肿瘤细胞生长。
• (-)-Epigallocatechin Gallate Derivatives for Inhibiting Proteasome
  申请人：CHAN Tak-Hang

  公开号：US20120232135A1

  公开（公告）日：2012-09-13

  A method of reducing tumor cell growth, the method including administering an effective amount of a compound having the formula:

  一种减少肿瘤细胞生长的方法，包括给予一种具有以下化学式的化合物的有效剂量：
• (−)-Epigallocatechin gallate derivatives for inhibiting proteasome
  申请人：The Hong Kong Polytechnic University

  公开号：US09169230B2

  公开（公告）日：2015-10-27

  A method of reducing tumor cell growth, the method including administering an effective amount of a compound having the formula:

  一种减少肿瘤细胞生长的方法，包括给予具有以下公式的化合物的有效量：
• US8193377B2
  申请人：——

  公开号：US8193377B2

  公开（公告）日：2012-06-05