(E)-4-phenylbutyl 3-(3,4-dihydroxyphenyl)acrylate

• 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: (E)-4-phenylbutyl 3-(3,4-dihydroxyphenyl)acrylate
• 英文别名: 4-phenylbutyl caffeate；4-phenylbutyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: BVIAYMYSSJEIMF-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-phenylbutyl 3-(3,4-dihydroxyphenyl)acrylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以93%的产率得到4-phenylbutyl 3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  WO2017/147718

  摘要：

  公开号：
• 作为产物：
  描述：

  TRANS-咖啡酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 (E)-4-phenylbutyl 3-(3,4-dihydroxyphenyl)acrylate
  参考文献：
  名称：

  Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line

  摘要：

  Caffeic acid phenethyl ester (CAPE, 2) and its twenty analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02 muM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10 mug/mL towards murine colon 26-L5 carcinoma cells. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00138-4

文献信息

• Synthesis of Diverse Hydroxycinnamoyl Phenylethanoid Esters Using<i>Escherichia coli</i>
  作者：Min Kyung Song、A Ra Cho、GeunYoung Sim、Joong-Hoon Ahn

  DOI：10.1021/acs.jafc.9b00041

  日期：2019.2.20

  p-coumaroyl tyrosol and CAPE, were also synthesized from glucose using engineered E. coli by introducing genes for the synthesis of substrates. Consequently, we synthesized approximately 393.4 mg/L p-coumaroyl tyrosol and 23.8 mg/L CAPE with this approach. Overall, these findings demonstrate that the rice PMT and 4CL proteins can be used for the synthesis of diverse hydroxycinnamoyl phenylethanoid esters owing

  咖啡酸苯乙基酯（CAPE）是羟基肉桂酸（苯基丙烷）和苯基乙醛类化合物（2-苯基乙醇; 2-PE）的酯，长期以来一直在传统医学中使用。在这里，我们通过将64种羟基肉桂酸和苯基乙醇的组合物喂入带有水稻基因OsPMT和Os4CL的大肠杆菌中，从而合成了54种羟基肉桂酸-苯乙醛酸酯。将相同的方法应用于咖啡酸和八种不同的苯醇的酯合成。还使用工程化的大肠杆菌从葡萄糖合成了两种羟基肉桂酰基苯乙基酯，对香豆酰基酪醇和CAPE 。通过引入用于合成底物的基因。因此，通过这种方法，我们合成了约393.4 mg / L对-香豆酰基酪醇和23.8 mg / L CAPE。总体而言，这些发现表明，大米的PMT和4CL蛋白由于其混杂性而可用于合成各种羟基肉桂酰基苯基乙醛酸酯，因此有必要进一步探索这些化合物的生物学活性。
• Synthesis and characterization of CAPE derivatives as xanthine oxidase inhibitors with radical scavenging properties
  作者：Wonbeen Choi、Valente Villegas、Hannah Istre、Ben Heppler、Niki Gonzalez、Nicole Brusman、Lindsey Snider、Emily Hogle、Janelle Tucker、Alma Oñate、Sandra Oñate、Lili Ma、Stefan Paula

  DOI：10.1016/j.bioorg.2019.02.049

  日期：2019.5

  of the enzyme xanthine oxidase (XO) with radical scavenging properties hold promise as novel agents against reperfusion injuries after ischemic events. By suppressing the formation of damaging reactive oxygen species (ROS) by XO or scavenging ROS from other sources, these compounds may prevent a buildup of ROS in the aftermath of a heart attack or stroke. To combine these two properties in a single molecule

  具有自由基清除特性的黄嘌呤氧化酶（XO）酶抑制剂有望作为抵抗缺血事件后再灌注损伤的新型药物。通过抑制XO破坏性活性氧（ROS）的形成或从其他来源清除ROS，这些化合物可预防心脏病发作或中风后ROS的积聚。为了在单个分子中结合这两个特性，我们使用方便的微波辅助Knoevenagel缩合方案合成并表征了非嘌呤XO抑制剂咖啡酸苯乙酯（CAPE）和19种衍生物。系统地改变两个苯环上羟基的数量和位置，我们基于实验确定的XO抑制数据得出了结构活性关系。分子对接表明，关键的酶/抑制剂相互作用涉及酚类抑制剂环与Tyr914之间的π-π相互作用，抑制剂羟基与Glu802之间的氢键以及CAPE苯环与位于肽入口的非极性残基之间的疏水相互作用。结合位点。为了有效清除稳定的自由基DPPH，在苯环的1,2-或1,4-位需要两个羟基。在所有测试的化合物中，E-苯基3-（3,4-二羟基苯基）丙烯酸酯（一种不带乙基醚的CA
• Synthesis and antitumor activity of feruloyl and caffeoyl derivatives
  作者：Hui-zhen Chen、You-bao Chen、Ya-ping Lv、Fang Zeng、Juan Zhang、Yong-lie Zhou、Han-bing Li、Li-fei Chen、Bin-jie Zhou、Jian-rong Gao、Chun-nian Xia

  DOI：10.1016/j.bmcl.2014.08.024

  日期：2014.9

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.
• MODULATORS OF LIPOXYGENASE AND CYCLOOXYGENASE ENZYME ACTIVITY
  申请人：Universite De Moncton

  公开号：EP3423429A1

  公开（公告）日：2019-01-09
• COMPOSITIONS AND METHODS FOR INHIBITING BLOOD CANCER CELL GROWTH
  申请人：UNIVERSITY OF NEW BRUNSWICK

  公开号：US20220211653A1

  公开（公告）日：2022-07-07

  Methods, compositions and uses for inhibiting the growth in blood cancer cells in a patient with one or more of a caffeic acid phenpropyl ester (GL8) analogue selected from the group consisting of As26, J229, J91, LL27, LL23, HM7, As25, MT26, and J205. The blood cancer cells can be myeloma, lymphoma and leukemia cells. The methods, compositions and uses can be in conjunction with the use of an IMiD to treat a patient. The compositions can include a pharmaceutically acceptable carrier, adjuvant or vehicle, a pharmaceutically acceptable salt or dietary supplement.