3,4-diacetyl phenethyl caffeate | 118971-54-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,4-diacetyl phenethyl caffeate
• 英文别名: (E)-4-(3-oxo-3-phenethoxyprop-1-enyl)-1,2-phenylene diacetate；2-phenylethyl (E)-3-(3,4-diacetoxyphenyl)propenate；2-phenylethyl (E)-3-(3,4-diacetyloxyphenyl)prop-2-enoate
• CAS: 118971-54-3
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: ZYZMRZIODPGYSO-PKNBQFBNSA-N

物化性质

• 沸点：
  533.0±50.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-diacetyl phenethyl caffeate 在 甲基叔丁基醚 、 sodium sulfate 、 异丙醇 作用下， 反应 4.0h， 以143 mg的产率得到咖啡酸苯乙酯
  参考文献：
  名称：

  从生咖啡豆提取物中化学酶法半合成咖啡酸 β-苯乙酯，蜂胶中的抗氧化成分。

  摘要：

  咖啡酸 β-苯乙酯 (CAPE) 是一种从蜂胶中分离出来的抗氧化生物活性儿茶酚，它是从生（未烘焙）罗布斯塔咖啡 (Coffea canephora) 豆提取物中的绿原酸和相关化合物中分 5 个步骤半合成的，总产量为 31 %。通过在连二亚硫酸钠 (Na2S2O4) 存在下绿原酸的碱性水解和通过南极念珠菌脂肪酶 B 介导的酯交换对儿茶酚二乙酸前体的脱保护作为最后一步来防止中间体和目标分子的氧化降解。

  DOI：

  10.1093/bbb/zbaa077
• 作为产物：
  描述：

  TRANS-咖啡酸 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 3,4-diacetyl phenethyl caffeate
  参考文献：
  名称：

  Synthesis and structure–activity relationship study of substituted caffeate esters as antinociceptive agents modulating the TREK-1 channel

  摘要：

  The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs. It has been reported that TREK-1 -/- mice were more sensitive than wild-type mice to painful stimuli, suggesting that activation of TREK-1 could result in pain inhibition. Here we report the synthesis of a series of substituted caffeate esters (12a-u) based on the hit compound CDC 2 (cinnamyl 3,4-dihydroxyl-alpha-cyanocinnamate). These analogs were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid induced-writhing assay) leading to the identification a series of novel molecules able to activate TREK-1 and displaying potent analgesic activity in vivo. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.049

文献信息

• CAFFEIC ACID DERIVATIVES AND THEIR USE IN IMPROVING NEURONAL CELL VIABILITY
  申请人：Liu Junyi

  公开号：US20120129931A1

  公开（公告）日：2012-05-24

  This invention relates to caffeic acid derivatives and improving viability of neuronal cells by contacting neuronal cells by caffeic acid derivatives as shown in the specification.

  本发明涉及咖啡酸衍生物，并通过与咖啡酸衍生物接触神经元细胞来提高神经元细胞的存活能力，如规范中所示。
• COMBINATION THERAPY
  申请人：Chemigen

  公开号：EP2629766B1

  公开（公告）日：2017-02-22
• USE OF PHENETHYL CAFFEATE DERIVATIVES IN THE PREPARATION OF A MEDICAMENT AGAINST TUMOR ANGIOGENESIS
  申请人：Liu Junyi

  公开号：US20130303611A1

  公开（公告）日：2013-11-14

  Disclosed is the use of the compounds represented by formula (I) in the preparation of a medicament against tumor angiogenesis, wherein R 1 and R 2 are each independently C 1 -C 8 alkylidene group or C 2 -C 8 alkenylidene group; A 1 and A 2 are each independently aryl, isoaryl, or aryl or isoaryl optionally substituted by halogen, —CN, —NO 2 , —OH, —SH, —OR 3 , —SR 3 , —R 3 , —R 3 —OR 4 , —C(O)R 3 , —S(O)R 3 , —S(O) 2 R 3 , —NR 4 R 5 , —C(O)OR 3 , —C(O)NR 4 R 5 , —O(O)CR 4 , —S(O)CR 4 or —NR 4 (O)CR 5 , wherein R 3 is C 1 -C 4 alkyl, R 4 and R 5 are each independently hydrogen, C 1 -C 4 alkyl, aryl or substituted aryl; and X and Y are each independently oxygen; and the compound of formula (I) does not include phenethyl caffeate.
• US8993621B2
  申请人：——

  公开号：US8993621B2

  公开（公告）日：2015-03-31
• US9040579B2
  申请人：——

  公开号：US9040579B2

  公开（公告）日：2015-05-26