(E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one | 133045-55-3

• 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: (E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one
• 英文别名: (E)-1-(3,4-dihydroxyphenyl)-6-phenylhex-1-en-3-one
• CAS: 133045-55-3
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: BKOOGPJYPVGVMG-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one 、 乙酸酐 在 吡啶 作用下， 以96%的产率得到acetic acid (E)-2-acetoxy-5-(3-oxo-6-phenyl-hex-1-enyl)phenyl ester
  参考文献：
  名称：

  Synthesis and neuroprotective effect of E-3,4-dihydroxy styryl aralkyl ketones derivatives against oxidative stress and inflammation

  摘要：

  E-3,4-Dihydroxy styryl aralkyl ketones as well as their 3,4-diacetylated derivatives as the analogues of neuroprotective agent CAPE were designed and synthesized for improving stability and lipid solubility. The neuroprotective activities of target compounds 10a-g and 11a-g were tested by three models in vitro, including 1,1-diphenyl-2-picrylhydrazyl radical scavenging capacity, neuronal protecting effect against damage induced by H2O2 in PC12 cells and nitric oxide suppression effect in BV2 microglial cells. The results demonstrated that compounds 10f and 11f exhibited the most potent neuroprotective effect against oxidative stress and inflammation, which is higher than that of the lead compound CAPE. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.016
• 作为产物：
  描述：

  5-苯基-3-戊烯-2-酮 在 四氢吡咯 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one
  参考文献：
  名称：

  Synthesis and neuroprotective effect of E-3,4-dihydroxy styryl aralkyl ketones derivatives against oxidative stress and inflammation

  摘要：

  E-3,4-Dihydroxy styryl aralkyl ketones as well as their 3,4-diacetylated derivatives as the analogues of neuroprotective agent CAPE were designed and synthesized for improving stability and lipid solubility. The neuroprotective activities of target compounds 10a-g and 11a-g were tested by three models in vitro, including 1,1-diphenyl-2-picrylhydrazyl radical scavenging capacity, neuronal protecting effect against damage induced by H2O2 in PC12 cells and nitric oxide suppression effect in BV2 microglial cells. The results demonstrated that compounds 10f and 11f exhibited the most potent neuroprotective effect against oxidative stress and inflammation, which is higher than that of the lead compound CAPE. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.016

文献信息

• Structure-activity relationship of caffeic acid phenethyl ester analogs as new 5-lipoxygenase inhibitors
  作者：Jérémie A. Doiron、Luc M. Leblanc、Martin J. G. Hébert、Natalie A. Levesque、Aurélie F. Paré、Jacques Jean-François、Marc Cormier、Marc E. Surette、Mohamed Touaibia

  DOI：10.1111/cbdd.12874

  日期：2017.4

  lipid mediators implicated in numerous inflammatory disorders. Caffeic acid phenethyl ester (CAPE) possesses potent anti-LTs activity through the inhibition of 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of LTs. In this study, we describe the design and synthesis of CAPE analogs as radical scavengers and 5-LO inhibitors. Caffeic esters bearing propargyl and allyl linkers between the caffeoyl

  白三烯（LTs）是一类脂质介体，与多种炎症性疾病有关。咖啡酸苯乙酯（CAPE）通过抑制5-脂氧合酶（5-LO）（LTs生物合成中的关键酶）而具有强大的抗LTs活性。在这项研究中，我们描述了作为自由基清除剂和5-LO抑制剂的CAPE类似物的设计和合成。通过Sonogashira和Heck交叉偶联反应合成了在咖啡酰基和芳基部分之间分别带有炔丙基和烯丙基连接基的咖啡酸酯（分别为4a-i和5a-i），以研究柔韧性和芳基取代对5-LO抑制的影响。合成了咖啡酰醇和醚（6，7a-b）以及咖啡酰醛和酮（8a-e），以阐明酯键对抑制活性的重要性。所有测试的化合物均被证明是良好的自由基清除剂（IC50为10-30μM）。在HEK293细胞模型中初步筛选抗LTs活性后，在人多形核白细胞（PMNL）中确定了所选化合物的5-LO抑制潜能。在PMNL的浓度依赖性测定中，大多数被筛选的化合物的性能均优于CAPE 3，其
• MEDICAL PRODUCT CONTAINING ACTIVE COMPONENT OF PROPOLIS OR GRAPEFRUIT SEED EXTRACT AND MANUFACTURING METHOD THEREOF
  申请人：CHANG Jeong Ho

  公开号：US20130129808A1

  公开（公告）日：2013-05-23

  A medical product containing either an active ingredient of propolis which is a natural antibiotic or a grapefruit seed extract, and a manufacturing method thereof are provided. The medical product is impregnated with a solution of CAPE (caffeic acid phenethyl ester) or pinocembrin, which is an active ingredient of propolis having antibacterial effects, to increase the antibacterial activity of the medical product due to antibacterial compounds contained in the active component, or the medical product is impregnated with a solution of a grapefruit seed extract such that the extract can exhibit antibacterial activity in the medical product.
• 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.
• US9044526B2
  申请人：——

  公开号：US9044526B2

  公开（公告）日：2015-06-02
• [EN] COMPOSITIONS AND METHODS FOR INHIBITING BLOOD CANCER CELL GROWTH<br/>[FR] COMPOSITIONS ET MÉTHODES POUR INHIBER LA CROISSANCE DE CELLULES SANGUINES CANCÉREUSES
  申请人：UNIV NEW BRUNSWICK

  公开号：WO2020210920A1

  公开（公告）日：2020-10-22

  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.