(E)-isopentyl 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)-isopentyl 3-(3,4-dihydroxyphenyl)acrylate
• 英文别名: isopentyl (E)-3-(3,4-dihydroxyphenyl)acrylate；isopentyl caffeate；3-methylbutyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ARDWPGKUNNUACS-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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)-isopentyl 3-(3,4-dihydroxyphenyl)acrylate 、 阿司匹林 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到isopentyl (E)-3-[3,4-bis(2-acetoxybenzoyloxy)phenyl]acrylate
  参考文献：
  名称：

  Design and Synthesis of Novel Aspirin-Caffeic Acid Ester Hybrids for Cardioprotection with Reduced Risk of Hemorrhagic Stroke

  摘要：

  一系列新型阿司匹林-咖啡酸酯杂合体被设计并合成为降低出血性卒中风险的护心药物，灵感来自NCX-4016。通过ADP诱导的体外抗血小板聚集和DPPH试验测定了所合成化合物中能够被酯酶如NCX 4016在体内释放的咖啡酸酯的抗氧化活性。结果显示，化合物3d展现出了比阿司匹林及其中间体咖啡酸异丙酯（2d）更强的抗血小板活性，而且表现出良好的抗氧化活性，因而可被认为是降低出血性卒中风险的新型高效护心药物候选者。

  DOI：

  10.14233/ajchem.2015.17896
• 作为产物：
  描述：

  异戊醇 、 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 生成 (E)-isopentyl 3-(3,4-dihydroxyphenyl)acrylate
  参考文献：
  名称：

  Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation

  摘要：

  The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C-12-caffeate), 11 (C-16-caffeate), 21 (C-8-ferulate), and 23 (C-12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 mu g/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 mu g/mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 mu g/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 mu g/mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C-4-C-12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C-3-C-8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 mu g/mL. Long-chain caffeates 11-14 (C-16-C-22) and short-chain ferulates 15-20 (C-3-C-5) were the most active in lipid peroxidation inhibition and showed 6070% activity at 5 mu g/mL concentration.

  DOI：

  10.1021/jf060899p

文献信息

• Design, Synthesis, and Preliminary Evaluation of Substituted Cinnamic Acid Esters as Selective Matrix Metalloproteinase Inhibitors
  作者：Zhi-Hao Shi、Nian-Guang Li、Qian-Ping Shi、Hao-Tang、Yu-Ping Tang

  DOI：10.1002/ddr.21015

  日期：2012.9

  Strategy, Management and Health Policy Preclinical Research

  战略，管理与卫生政策 临床前研究
• A Rapid and Practical Catalytic Esterification for the Preparation of Caffeic Acid Esters
  作者：Dongsheng Xie、Fengzhi Yang、Jin Xie、Man Zhang、Wenlu Liu、Lei Fu

  DOI：10.3184/174751914x14146000527920

  日期：2014.11

  A convenient and practical catalytic method for the preparation of caffeic acid esters is reported. This esterification was carried out with high efficiency in the presence of ytterbium triflate in nitromethane without any other auxiliary reagents. The wide scope of application and especially the higher reactivity and more convenient procedure than previous methods make it a valuable application for the synthesis of caffeic acid esters and other cinnamic acid esters.

  报告中介绍了一种方便实用的催化方法来制备咖啡酸酯。这种酯化反应是在硝基甲烷中三酸镱的存在下高效进行的，无需任何其他辅助试剂。与以前的方法相比，该方法应用范围广，特别是反应活性更高，操作过程更简便，因此在合成咖啡酸酯和其他肉桂酸酯方面具有重要的应用价值。
• [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。
• MODULATORS OF LIPOXYGENASE AND CYCLOOXYGENASE ENZYME ACTIVITY
  申请人：Universite de Moncton

  公开号：US20190119194A1

  公开（公告）日：2019-04-25

  The present invention relates to modulators of lipoxygenase and/or cyclooxygenase enzyme. The present invention also provides compositions comprising such modulators, and methods therewith for treating lipoxygenase receptor mediated diseases.
• Design and Synthesis of Novel Aspirin-Caffeic Acid Ester Hybrids for Cardioprotection with Reduced Risk of Hemorrhagic Stroke
  作者：Zhi-Hao Shi、Nian-Guang Li、Yu-Ping Tang、Qian-Ping Shi、Wei Zhang、Peng-Xuan Zhang、Ze-Xi Dong、Wei Li、Jin-Ao Duan

  DOI：10.14233/ajchem.2015.17896

  日期：——

  A series of novel aspirin-caffeic acid ester hybrids for cardioprotection with reduced risk of hemorrhagic stroke were designed and synthesized by coupling aspirin and caffeic acid esters inspired by NCX-4016. The synthesized compounds were evaluated for their in vitro antiplatelet aggregations induced by ADP and antioxidant activity of the caffeic acid esters which could be released from the hybrids by esterases in vivo like NCX 4016 were determined by DPPH assay. The results showed that compound 3d exhibited potent antiplatelet activity than aspirin and its intermediate caffeic acid isopropyl ester (2d) showed good antioxidant activity and thus could be considered to be novel potent cardioprotectic drug candidates with reduced risk of hemorrhagic stroke.

  一系列新型阿司匹林-咖啡酸酯杂合体被设计并合成为降低出血性卒中风险的护心药物，灵感来自NCX-4016。通过ADP诱导的体外抗血小板聚集和DPPH试验测定了所合成化合物中能够被酯酶如NCX 4016在体内释放的咖啡酸酯的抗氧化活性。结果显示，化合物3d展现出了比阿司匹林及其中间体咖啡酸异丙酯（2d）更强的抗血小板活性，而且表现出良好的抗氧化活性，因而可被认为是降低出血性卒中风险的新型高效护心药物候选者。