肉桂咖啡酸 | 115610-32-7

• 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
• 中文名称: 肉桂咖啡酸
• 英文名称: (2E)-cinnamyl 3-(3,4-dihydroxyphenyl)acrylate
• 英文别名: (E)-cinnamyl 3-(3,4-dihydroxyphenyl)acrylate；(E)-cinnamyl-(E)-caffeate；cinnamyl caffeate；[(E)-3-phenylprop-2-enyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 115610-32-7
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: GRZQNEYQRVPNRY-WUZDHUPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  2-8℃

制备方法与用途

cinnamyl caffeate 是一种从斯洛文尼亚蜂胶中提取的咖啡酸酯。

反应信息

• 作为反应物：
  描述：

  肉桂咖啡酸 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3-phenylpropyl 3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441
• 作为产物：
  描述：

  (E)-3-(3,4-bis(methoxymethoxy)phenyl)acrylic acid 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 肉桂咖啡酸
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441

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
• Derivatives of Propane Diyl Dicinnamate
  申请人：MACGREGOR ALEXANDER

  公开号：US20110086912A1

  公开（公告）日：2011-04-14

  The present invention provides a method for treating a cancer in a subject involving administering to the subject a compound of formula (II) or (II′): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are independently H, OH, alkylcarbonyloxy, or a pharmaceutically acceptable salt thereof. Also provided is a compound of formula (II) or (II)′, wherein R 1 and R 2 are independently OH, alkoxy or alkylcarbonyloxy, R 3 and R 4 are independently H, OH, alkoxy or alkylcarbonyloxy, R 6 is H, alkoxy or alkylcarbonyloxy, R 5 is H, OH or alkylcarbonyloxy, R 6 is H or alkoxy, and R 7 is H, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗受试者癌症的方法，涉及向受试者施用以下化合物的公式(II)或(II′)：其中R1、R2、R3、R4、R5、R6和R7独立地为H、OH、烷基羰基氧基或其药用可接受盐。还提供了一种公式(II)或(II′)的化合物，其中R1和R2独立地为OH、烷氧基或烷基羰基氧基，R3和R4独立地为H、OH、烷氧基或烷基羰基氧基，R6为H、烷氧基或烷基羰基氧基，R5为H、OH或烷基羰基氧基，R6为H或烷氧基，R7为H或其药用可接受盐。
• Derivatives of propane diyl dicinnamate
  申请人：ORX PHARMACEUTICAL CORPORATION

  公开号：US10052301B2

  公开（公告）日：2018-08-21

  The present invention provides a method for treating a cancer in a subject involving administering to the subject a compound of formula (II) or (II′): wherein R1, R2, R3, R4, R5, R6 and R7 are independently H, OH, alkoxy or alkylcarbonyloxy, or a pharmaceutically acceptable salt thereof. Also provided is a compound of formula (II) or (II)′, wherein R1 and R2 are independently OH, alkoxy or alkylcarbonyloxy, R3 and R4 are independently H, OH, alkoxy or alkylcarbonyloxy, R6 is H, alkoxy or alkylcarbonyloxy, R5 is H, OH or alkylcarbonyloxy, R6 is H or alkoxy, and R7 is H, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗受试者癌症的方法，包括向受试者施用式(II)或(II′)化合物： 其中R1、R2、R3、R4、R5、R6和R7独立地为H、OH、烷氧基或烷基羰氧基，或其药学上可接受的盐。还提供了式 (II) 或 (II)′ 的化合物，其中 R1 和 R2 独立地为 OH、烷氧基或烷基羰基氧基，R3 和 R4 独立地为 H、OH、烷氧基或烷基羰基氧基，R6 为 H、烷氧基或烷基羰基氧基，R5 为 H、OH 或烷基羰基氧基，R6 为 H 或烷氧基，R7 为 H，或其药学上可接受的盐。
• [EN] DRUG FOR TREATING ARTERY-RELATED DISEASES, AND USE THEREOF<br/>[FR] MÉDICAMENT POUR LE TRAITEMENT DE MALADIES ARTÉRIELLES ET SON UTILISATION<br/>[ZH] 用于治疗动脉相关疾病的药物及其用途
  申请人：SHANGHAI INST MATERIA MEDICA CAS

  公开号：WO2021063366A1

  公开（公告）日：2021-04-08

  提供用于治疗动脉相关疾病的药物及其用途。具体地，提供了一类式I化合物在治疗动脉相关疾病中的应用。实验表明，式I化合物对动脉瘤、壁间血肿和/或动脉夹层有显著疗效。
• Mali; Papalkar, Journal of Chemical Research - Part S, 2001, # 10, p. 433 - 435
  作者：Mali、Papalkar

  DOI：——

  日期：——