(E)-3-(3,4-dihydroxyphenyl)-N-octylacrylamide | 136944-15-5

• 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-octylacrylamide
• 英文别名: 3,4-dihydroxycinnamic acid n-octyl amide；caffeic acid octyl amide；Caffeic acid octylamide；N-octyl caffeamide；(E)-3-(3,4-dihydroxyphenyl)-N-octylprop-2-enamide
• CAS: 136944-15-5
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: DWBPZEWVSALRKR-PKNBQFBNSA-N

物化性质

• 沸点：
  518.5±50.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  TRANS-咖啡酸 生成 (E)-3-(3,4-dihydroxyphenyl)-N-octylacrylamide
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Inhibitory activities and inhibition specificities of caffeic acid derivatives and related compounds toward 5-lipoxygenase.
  作者：Masanori SUGIURA、Youichiro NAITO、Yasunari YAMAURA、Chikara FUKAYA、Kazumasa YOKOYAMA

  DOI：10.1248/cpb.37.1039

  日期：——

  Various caffeic acid derivatives were synthesized, and their effects on 5-lipoxygenase (5-LO), 12-lipoxygenase (12-LO) and prostaglandin (PG) synthase activities were investigated. Among them, caffeic acid octyl amide (5) and 1-(3, 4-dihydroxyphenyl)-1-octen-3-one (11) showed very potent inhibitory activities toward 5-LO with IC50 values of 4.2×10-8 and 3.5×10-8 M, respectively. They were very selective inhibitors for 5-LO. Compound 11 showed noncompetitive inhibition, and the two adjacent hydroxy groups attached to the benzene ring, as well as the hydrophobic alkyl side chain, were required for its strong binding to 5-LO.

  合成了多种咖啡酸衍生物，并研究了它们对5-脂氧合酶（5-LO）、12-脂氧合酶（12-LO）和前列腺素（PG）合成酶活性的影响。其中，咖啡酸辛酰胺（5）和1-(3, 4-二羟基苯基)-1-辛烯-3-酮（11）对5-LO显示出非常强的抑制活性，IC50值分别为4.2×10-8 M和3.5×10-8 M。它们是非常选择性的5-LO抑制剂。化合物11表现出非竞争性抑制作用，苯环上的两个相邻羟基以及疏水性的烷基侧链对其与5-LO的强结合是必需的。
• [EN] CAFFEIC ACID DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS D'ACIDE CAFÉIQUE ET LEURS UTILISATIONS
  申请人：MUSC FOUND FOR RES DEV

  公开号：WO2017161093A1

  公开（公告）日：2017-09-21

  The present invention relates to compounds of formula (I): including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.

  本发明涉及公式(I)的化合物，包括其任何立体化异构体，或其药用可接受的盐，用于治疗结核病。
• METHOD OF TREATING OR PREVENTING HYPERLIPIDEMIA WITH CAFFEAMIDE DERIVATIVES
  申请人：Shih Chun-Ching

  公开号：US20170014400A1

  公开（公告）日：2017-01-19

  The present invention provides a method of treating or preventing hyperlipidemia in a subject in need thereof. Such method includes, specifically, administrating to the subject a therapeutically effective amount of a caffeamide derivative. The present invention also provides a pharmaceutical composition containing, primarily, the caffeamide derivative. The method and pharmaceutical composition of the present invention can effectively and significantly lower the high-fat diet-induced body weight gain and absolute visceral fat weight as well as the concentration of triglycerides and free fatty acids in blood, and levels of total lipid and triacylglycerol in liver tissue. In addition, the caffeamide of the present invention also reduces size of adipocyte, hepatocellular ballooning phenomenon, and liver steatosis. Through promotion of phosphorylation of 5′ adenosine monophosphate-activated protein kinase (AMPK) in muscle and liver, the caffeamide derivatives of the present invention is suitable for ameliorating or remedying hyperlipidemia.

  本发明提供了一种治疗或预防高脂血症的方法。该方法具体包括向需要治疗的主体施用治疗有效量的咖啡酰胺衍生物。本发明还提供了一种主要含有咖啡酰胺衍生物的制药组合物。本发明的方法和制药组合物可以有效地和显著地降低高脂饮食引起的体重增加和绝对内脏脂肪重量，以及血液中甘油三酯和游离脂肪酸的浓度，以及肝组织中总脂质和三酰甘油的水平。此外，本发明的咖啡酰胺还可以减小脂肪细胞的大小、肝细胞球形变现象和脂肪肝。通过促进肌肉和肝脏中5'腺苷酸单磷酸激活蛋白激酶（AMPK）的磷酸化，本发明的咖啡酰胺衍生物适用于改善或治疗高脂血症。
• 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
• A lipoxygenase inhibitor
  申请人：GREEN CROSS CORPORATION

  公开号：EP0163270A2

  公开（公告）日：1985-12-04

  A lipoxygenase inhibitor comprising as active ingredient a substituted styrene derivative having a radical of the general formula wherein X denotes a hydroxyl group or a lower alkoxy group and q is an integer of 2 or 3, and containing carbon atoms in total of at least 8.

  一种脂氧合酶抑制剂，其活性成分包括具有通式基团的取代苯乙烯衍生物，其中 X 表示羟基或低级烷氧基，q 为 2 或 3 的整数，且总共含有至少 8 个碳原子。