(E)-3-(3,4-dihydroxyphenyl)-N-decylacrylamide | 136944-16-6

• 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-decylacrylamide
• 英文别名: 3,4-dihydroxycinnamic acid n-decyl amide；caffeic acid decyl amide；Caffeic acid decylamide；(E)-N-decyl-3-(3,4-dihydroxyphenyl)prop-2-enamide
• CAS: 136944-16-6
• 化学式: C₁₉H₂₉NO₃
• 分子量: 319.444
• InChiKey: YUSYUVAGPQEJDN-ACCUITESSA-N

物化性质

• 沸点：
  536.5±50.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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-decylacrylamide
  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。
• 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。
• Pharmaceutical composition containing slightly water-soluble drug
  申请人：THE GREEN CROSS CORPORATION

  公开号：EP0448091A2

  公开（公告）日：1991-09-25

  The orally administrable pharmaceutical compositions containing a slightly water-soluble drug, characterized by improved stability and improved absorption of the drug from digestive tract into blood. The use of the compositions of the present invention enables decrease of the dose amount of a slightly water-soluble drug, which eventually leads to alleviation of pains and side effects on the part of patients.

  本发明的口服药物组合物含有微水溶性药物，其特点是稳定性更好，药物从消化道进入血液的吸收率更高。使用本发明的组合物可以减少微水溶性药物的剂量，从而最终减轻患者的痛苦和副作用。