(2E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)propenamide | 91000-11-2

• 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: (2E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)propenamide
• 英文别名: (E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide；N-(E)-feruloylputrescine；N-feruloylputrescine；feruloylputrescine；ferulylputrescine；Feruloylputrescin；(E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• CAS: 91000-11-2
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: SFUVCMKSYKHYLD-FNORWQNLSA-N

物化性质

• 沸点：
  511.5±50.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

N-乙酰基肉桂酰肌氨酸是一种可以在木兰属植物中分离出的生物碱。

反应信息

• 作为反应物：
  描述：

  (2E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)propenamide 、 3-amino-5,7-dimethyltricyclo[3.3.1.1^3,7]decane-1-carboxylic acid hydrochloride 在 1-羟基苯并三唑 、 1,2-二氯乙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.17h， 以48%的产率得到(E)-3-amino-N-(4-(3-(4-hydroxy-3-methoxyphenyl)acrylamido)butyl)-5,7-dimethyladamantane-1-carboxamide
  参考文献：
  名称：

  Merging memantine and ferulic acid to probe connections between NMDA receptors, oxidative stress and amyloid-β peptide in Alzheimer's disease

  摘要：

  N-methyl-D-aspartate receptors (NMDAR) are critically involved in the pathogenesis of Alzheimer's disease (AD). Acting as an open-channel blocker, the anti-AD drug memantine preferentially targets NMDAR overactivation, which has been proposed to trigger neurotoxic events mediated by amyloid beta peptide (A beta) and oxidative stress. In this study, we applied a multifunctional approach by conjugating memantine to ferulic acid, which is known to protect the brain from A beta neurotoxicity and neuronal death caused by ROS. The most interesting compound (7) behaved, like memantine, as a voltage-dependent antagonist of NMDAR (IC50 = 6.9 mu M). In addition, at 10 mu M concentration, 7 exerted antioxidant properties both directly and indirectly through the activation of the Nrf-2 pathway in SH-SY5Y cells. At the same concentration, differently from the parent compounds memantine and ferulic acid alone, it was able to modulate A beta production, as revealed by the observed increase of the non-amyloidogenic sAPP alpha in H4-SW cells. These findings suggest that compound 7 may represent a promising tool for investigating NMDAR-mediated neurotoxic events involving A beta burden and oxidative damage. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.07.011
• 作为产物：
  描述：

  tert-butyl (E)-(4-(3-(4-hydroxy-3-methoxyphenyl)acrylamido)butyl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.5h， 以96%的产率得到(2E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)propenamide
  参考文献：
  名称：

  Merging memantine and ferulic acid to probe connections between NMDA receptors, oxidative stress and amyloid-β peptide in Alzheimer's disease

  摘要：

  N-methyl-D-aspartate receptors (NMDAR) are critically involved in the pathogenesis of Alzheimer's disease (AD). Acting as an open-channel blocker, the anti-AD drug memantine preferentially targets NMDAR overactivation, which has been proposed to trigger neurotoxic events mediated by amyloid beta peptide (A beta) and oxidative stress. In this study, we applied a multifunctional approach by conjugating memantine to ferulic acid, which is known to protect the brain from A beta neurotoxicity and neuronal death caused by ROS. The most interesting compound (7) behaved, like memantine, as a voltage-dependent antagonist of NMDAR (IC50 = 6.9 mu M). In addition, at 10 mu M concentration, 7 exerted antioxidant properties both directly and indirectly through the activation of the Nrf-2 pathway in SH-SY5Y cells. At the same concentration, differently from the parent compounds memantine and ferulic acid alone, it was able to modulate A beta production, as revealed by the observed increase of the non-amyloidogenic sAPP alpha in H4-SW cells. These findings suggest that compound 7 may represent a promising tool for investigating NMDAR-mediated neurotoxic events involving A beta burden and oxidative damage. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.07.011

文献信息

• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。
• Solid-phase synthesis and antibacterial activity of hydroxycinnamic acid amides and analogues against methicillin-resistant Staphylococcus aureus and vancomycin-resistant S. aureus
  作者：Boon-ek Yingyongnarongkul、Nuttapon Apiratikul、Nuntana Aroonrerk、Apichart Suksamrarn

  DOI：10.1016/j.bmcl.2006.08.062

  日期：2006.11

  A library of hydroxycinnamic acid amides (HCAAs) and analogues were synthesized using solid-phase synthesis technique. These compounds were screened for antibacterial against methicillin-resistant Staphylococcus aureus (MRSA) (11 strains) and vancomycin-resistant S. aureus (VRSA) (4 strains). Dihydrocaffeoyl analogues showed activity against VRSA which were better than the reference drugs, vancomycin and oxacillin. These compounds also exhibited antibacterial activity against MRSA, which were more potent than oxacillin. (c) 2006 Elsevier Ltd. All rights reserved.
• Malmberg, Alf, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 2, p. 153 - 156
  作者：Malmberg, Alf

  DOI：——

  日期：——
• An efficient systhesis of some biologically important monoacylated diamines
  作者：Gerhard Kunesch

  DOI：10.1016/s0040-4039(00)88399-9

  日期：1983.1
• KUNESCH, G.;MAURICETTE, S.;CHUILON, (NEE, MONNIER), A.;MARTIN, C.;MARTIN,+
  作者：KUNESCH, G.、MAURICETTE, S.、CHUILON, (NEE, MONNIER), A.、MARTIN, C.、MARTIN,+

  DOI：——

  日期：——