hexyl p-hydroxy-cinnamate

• 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: hexyl p-hydroxy-cinnamate
• 英文别名: trans-hexyl 3-(4-hydroxyphenyl)propenoate；(E)-hexyl 3-(4-hydroxyphenyl)acrylate；hexyl p-coumarate；hexyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: AGXFGQBFMFJFCD-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  hexyl p-hydroxy-cinnamate 在 氢氧化钾 作用下， 以 甲醇 、 苯 为溶剂， 生成 4-香豆酸 、 正己醇
  参考文献：
  名称：

  Enzymes Inhibitory Constituents From Buddleja Crispa

  摘要：

  从Buddleja crispa中分离出类固醇半乳糖苷1和芳基酯2和3，以及首次从该物种中分离出的ginipin 4、gardiol 5、1-辛醇 6和甲基苯甲酸酯7。通过光谱技术和化学研究确定了所有化合物的结构。类固醇半乳糖苷1是一种脂氧酶抑制剂。化合物1-3对丁酰胆碱酯酶显示了抑制活性，而化合物2和3进一步显示对乙酰胆碱酯酶的抑制作用。

  DOI：

  10.1515/znb-2005-0319
• 作为产物：
  描述：

  正己醇 在 吡啶 、 苯胺 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 4.0h， 生成 hexyl p-hydroxy-cinnamate
  参考文献：
  名称：

  Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold

  摘要：

  The number of people affected by neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease is rapidly increasing owing to the global increase in life expectancy. Small molecules with neurotrophic effects have great potential for management of these neurological disorders. In this study, different (C1–C12) alkyl ester derivatives of hydroxycinnamic acids (HCAs) were synthesized (a total of 30 compounds). The neurotrophic capacity of the test compounds was examined by measuring promotion of survival in serum‐deprived conditions and enhancement of nerve growth factor (NGF)‐induced neurite outgrowth in PC12 neuronal cells. p‐Coumaric, ferulic, and sinapic acids and their esters did not alter cell survival, while caffeic acid and all its alkyl esters, especially decyl and dodecyl caffeate, significantly promoted neuronal survival at 25 μm. Methyl, ethyl, propyl, and butyl caffeate esters also significantly enhanced NGF‐induced neurite outgrowth, among which the most effective ones were propyl and butyl esters, which at 5 μm led to 25‐ and 22‐fold increases in the number of neurites, respectively. The findings of the docking study suggested phosphatidylinositol 3‐kinase (PI3K) as the potential molecular target. In conclusion, our findings demonstrate that alkyl esters of caffeic acid can be useful as scaffolds for the discovery of therapeutic agents for neurodegenerative diseases.

  DOI：

  10.1111/cbdd.12829

文献信息

• Alkyl and Aryl Derivatives Based on p-Coumaric Acid Modification and Inhibitory Action against Leishmania braziliensis and Plasmodium falciparum
  作者：Susiany P. Lopes、Lina M. Yepes、Yunierkis Pérez-Castillo、Sara M. Robledo、Damião P. de Sousa

  DOI：10.3390/molecules25143178

  日期：——

  worldwide and are creating a public health problem. The present work evaluates the leishmanicidal and antiplasmodial action of a series of twelve p-coumaric acid derivatives. Of the tested derivatives, eight presented antiparasitic activities 1–3, 8–12. The hexyl p-coumarate derivative (9) (4.14 ± 0.55 μg/mL; selectivity index (SI) = 2.72) showed the highest leishmanicidal potency against the Leishmania

  在低收入人群中，被忽视的疾病是导致死亡的主要原因。其中，利什曼病和疟疾是寄生虫、原生动物感染，影响着全世界数百万人，并正在造成公共卫生问题。目前的工作评估了一系列十二种对香豆酸衍生物的杀利什曼原虫和抗疟原虫的作用。在测试的衍生物中，八种具有抗寄生虫活性 1-3、8-12。对香豆酸己酯衍生物 (9) (4.14 ± 0.55 μg/mL；选择性指数 (SI) = 2.72) 显示出对巴西利什曼原虫无鞭毛体形式的最高利什曼原虫杀灭效力。分子对接研究结果表明，该化合物抑制醛脱氢酶 (ALDH)、丝裂原活化激酶蛋白 (MPK4) 和 DNA 拓扑异构酶 2 (TOP2)，所有这些都是巴西利什曼原虫发育的关键酶。数据表明，这些酶通过范德华键、疏水相互作用和氢键与同一化合物的酚类和脂肪族部分相互作用。在分析的其他化合物中，对香豆酸甲酯 (64.59 ± 2.89 μg/mL；IS = 0.1) 显示出
• Isolation and Activity of<i>N</i>-<i>p</i>-Coumaroyltyramine, an<i>α</i>-Glucosidase Inhibitor in Welsh Onion (<i>Allium fistulosum</i>)
  作者：Tetsuo Nishioka、Jun Watanabe、Jun Kawabata、Ryoya Niki

  DOI：10.1271/bbb.61.1138

  日期：1997.1

  A phenolic amide, N-p-coumaroyltyramine (1), was isolated as an α-glucosidase inhibitor from methanol extracts of Welsh onion (Allium fistulosum). The inhibitory activity of 1 against a yeast enzyme was as high as Ki 8.4 × 10−7  m. From a structure-activity relationship study of 1 and its related compounds, the occurrence of α-glucosidase inhibitory activity required a p-coumaramide structure, with an amide hydrogen and alkyl or aralkyl substituent on the amide part.

  从威尔士洋葱（Allium fistulosum）的甲醇提取物中分离出一种酚酰胺--N-对香豆酰酪胺（1），作为一种α-葡萄糖苷酶抑制剂。通过对 1 及其相关化合物的结构-活性关系研究发现，α-葡萄糖苷酶抑制活性的产生需要对香豆酰酰胺结构，酰胺部分含有酰胺氢和烷基或芳烷基取代基。
• 一种对香豆酸酯及其合成方法与应用
  申请人：华南理工大学

  公开号：CN113402392B

  公开（公告）日：2023-04-28
• LIQUID CRYSTAL ALIGNMENT AGENT, LIQUID CRYSTAL ALIGNMENT FILM, AND LIQUID CRYSTAL DISPLAY ELEMENT
  申请人：Chi Mei Corporation

  公开号：US20170022419A1

  公开（公告）日：2017-01-26

  A liquid crystal alignment agent capable of forming a liquid crystal alignment film having good pre-tilt angle light stability, the liquid crystal alignment film, and a liquid crystal display element having the liquid crystal alignment film are provided. The liquid crystal alignment agent includes a polymer (A), a photosensitive polysiloxane (B), and a solvent (C). The polymer (A) is obtained by reacting a mixture, wherein the mixture includes a tetracarboxylic dianhydride component (a1) and a diamine component (a2). The diamine component (a2) includes a diamine compound (a2-1) represented by formula (1). The photosensitive polysiloxane (B) is obtained by reacting a silane compound (b1-1) containing an epoxy group and a cinnamic acid derivative (b2).
• Enzymes Inhibitory Constituents From Buddleja Crispa
  作者：Ijaz Ahmad、Abdul Malik、Nighat Afza、Itrat Anis、Itrat Fatima、Sarfraz Ahmad Nawaz、Rasool Bukhsh Tareen、M. Iqbal Choudhary

  DOI：10.1515/znb-2005-0319

  日期：2005.3.1

  Steroidal galactoside 1 and aryl esters 2 and 3 have been isolated from Buddleja crispa, along with ginipin 4, gardiol 5, 1-heptacosanol 6, and methyl benzoate 7, isolated for the first time from this species. The structures of all of the compounds were determined by spectroscopic techniques and chemical studies. The steroidal galactoside 1 is an inhibitor of lipoxygenase. Compounds 1- 3 displayed inhibitory activity against butyrylcholinesterse, while compounds 2 and 3 further showed inhibition against acetylcholinesterase

  从Buddleja crispa中分离出类固醇半乳糖苷1和芳基酯2和3，以及首次从该物种中分离出的ginipin 4、gardiol 5、1-辛醇 6和甲基苯甲酸酯7。通过光谱技术和化学研究确定了所有化合物的结构。类固醇半乳糖苷1是一种脂氧酶抑制剂。化合物1-3对丁酰胆碱酯酶显示了抑制活性，而化合物2和3进一步显示对乙酰胆碱酯酶的抑制作用。