(E)-3-(3,4-dihydroxyphenyl)-N-propylacrylamide

• 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)-3-(3,4-dihydroxyphenyl)-N-propylacrylamide
• 英文别名: N-propyl caffeamide；(E)-3-(3,4-dihydroxyphenyl)-N-propylprop-2-enamide
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: RUEAFFGYGBHHJS-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  正丙胺 、 TRANS-咖啡酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 以12.7%的产率得到(E)-3-(3,4-dihydroxyphenyl)-N-propylacrylamide
  参考文献：
  名称：

  天然抗氧化剂咖啡酸的衍生物，是发现新型非肽类神经营养剂的基础

  摘要：

  帕金森氏病和阿尔茨海默氏病等神经退行性疾病威胁着数百万人的生命，并且随着人口老龄化的增加，患病人数也在不断增加。小分子神经营养剂代表了用于神经退行性疾病的药理学管理的有前途的疗法。在这项研究中，一系列具有可变烷基链长度的咖啡酸酰胺类似物，包括ACAF3（C3），ACAF4（C4），ACAF6（C6），ACAF8（C8）和ACAF12（C12）合成，并通过不同方法在PC12神经元细胞中检查其神经营养活性。我们发现，通过MTT分析测定，在25μM的血清剥夺条件下，所有咖啡酰胺衍生物均能显着提高PC12神经元细胞的存活率。ACAF4，ACAF6和ACAF8当浓度为5 µM时，神经生长因子（NGF）诱导神经突增生（神经元分化的迹象）的效果也显着增强。酰胺衍生物的神经营养作用似乎不是由原肌球蛋白受体激酶A（TrkA）受体的直接激活介导的，因为有效的TrkA拮抗剂K252a并未阻断神经元存活的增强作用

  DOI：

  10.1016/j.bmc.2017.04.026

文献信息

• (E)-3-(3,4-dihydroxyphenyl)-N-(prop-2-yn-1-yl)acrylamide for treatment of neurodegenerative diseases
  申请人：THE UNIVERSITY OF HONG KONG

  公开号：US10259777B2

  公开（公告）日：2019-04-16

  The present invention pertains to a pharmaceutical composition comprising a pharmaceutically acceptable carrier and (E)-3-(3,4-dihydroxyphenyl)-N-(prop-2-yn-1-yl)acrylamide of Formula (I): The invention also pertains to a method for stimulating neurite outgrowth by administering to cells in the area where neurite outgrowth is desired a therapeutically effective amount of the compound of Formula (I). Further, the invention pertains to a method for attenuating neuron injury in a subject by contacting a neuron in a subject in need thereof with a therapeutically effective amount of the compound of Formula (I). Furthermore, a method of preparing the compound of Formula (I) are provided.

  本发明涉及一种药物组合物，它包含一种药学上可接受的载体和式（I）的(E)-3-(3,4-二羟基苯基)-N-(丙-2-炔-1-基)丙烯酰胺： 本发明还涉及一种刺激神经元生长的方法，即向需要神经元生长区域的细胞施用治疗有效量的式（I）化合物。此外，本发明还涉及一种减轻受试者神经元损伤的方法，方法是将治疗有效量的式（I）化合物与有需要的受试者的神经元接触。此外，还提供了制备式（I）化合物的方法。
• A Novel Neuroprotective and Neurorestorative N-Propargyl Caffeamide (PACA) and Use as A Treatment for Neurodegenerative Diseases
  申请人：THE UNIVERSITY OF HONG KONG

  公开号：US20180155275A1

  公开（公告）日：2018-06-07

  The present invention is directed to compounds, pharmaceutical compositions, and related methods of treatment and/or prevention for neurodegenerative diseases, such as Parkinson's disease.
• MONOMERS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME
  申请人：CORNELL UNIVERSITY

  公开号：US20200354319A1

  公开（公告）日：2020-11-12

  Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. in vivo) to form a multimer, (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding domains on a protein or on different proteins.
• [EN] COMPOSITIONS AND METHODS FOR TREATING MYOCARDIAL INFARCTION<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT DE L'INFARCTUS DU MYOCARDE
  申请人：UNIV HONG KONG

  公开号：WO2017197637A1

  公开（公告）日：2017-11-23

  Methods of treating inflammation conditions in a subject is provided, including administering to the subject an effective amount of one or more caffeic acid derivatives to effectively alter the polarization of macrophages from M1 to M2, i.e., from a pro-inflammatory phenotype to a reparative phenotype activation of macrophages. In some embodiments, the caffeic acid derivative is administered to treat myocardial infarction, attenuate the chemotaxis and phagocytosis of macrophages, increase the viability of cardiomyocytes in an ischemia-mimicking environment, and/or increase the activities of antioxidant enzymes in the tissues. In some embodiments, the caffeic acid derivatives have an improved half-life in plasma or pathophysiological conditions. A facile and cost-effective method of making these caffeic acid derivatives is also provided.
• Derivatives of caffeic acid, a natural antioxidant, as the basis for the discovery of novel nonpeptidic neurotrophic agents
  作者：Fatemeh Moosavi、Razieh Hosseini、Hamid Rajaian、Tiago Silva、Diogo Magalhães e Silva、Luciano Saso、Najmeh Edraki、Ramin Miri、Fernanda Borges、Omidreza Firuzi

  DOI：10.1016/j.bmc.2017.04.026

  日期：2017.6

  neurodegenerative diseases. In this study, a series of caffeic acid amide analogues with variable alkyl chain lengths, including ACAF3 (C3), ACAF4 (C4), ACAF6 (C6), ACAF8 (C8) and ACAF12 (C12) were synthesized and their neurotrophic activity was examined by different methods in PC12 neuronal cells. We found that all caffeic acid amide derivatives significantly increased survival in PC12 neuronal cells

  帕金森氏病和阿尔茨海默氏病等神经退行性疾病威胁着数百万人的生命，并且随着人口老龄化的增加，患病人数也在不断增加。小分子神经营养剂代表了用于神经退行性疾病的药理学管理的有前途的疗法。在这项研究中，一系列具有可变烷基链长度的咖啡酸酰胺类似物，包括ACAF3（C3），ACAF4（C4），ACAF6（C6），ACAF8（C8）和ACAF12（C12）合成，并通过不同方法在PC12神经元细胞中检查其神经营养活性。我们发现，通过MTT分析测定，在25μM的血清剥夺条件下，所有咖啡酰胺衍生物均能显着提高PC12神经元细胞的存活率。ACAF4，ACAF6和ACAF8当浓度为5 µM时，神经生长因子（NGF）诱导神经突增生（神经元分化的迹象）的效果也显着增强。酰胺衍生物的神经营养作用似乎不是由原肌球蛋白受体激酶A（TrkA）受体的直接激活介导的，因为有效的TrkA拮抗剂K252a并未阻断神经元存活的增强作用