decyl p-coumarate | 1173709-48-2

• 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: decyl p-coumarate
• 英文别名: 4-hydroxycinnamic acid decyl ester；trans-decyl 3-(4-hydroxyphenyl)propenoate；(E)-decyl 3-(4-hydroxyphenyl)acrylate；decyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 1173709-48-2
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: BXCDXYBBFPCRDB-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  癸醇 在 吡啶 、 苯胺 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 4.0h， 生成 decyl p-coumarate
  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

• Synthesis and DNA Polymerase .ALPHA. and .BETA. Inhibitory Activity of Alkyl p-Coumarates and Related Compounds
  作者：Katsumi Nishimura、Yukiko Takenaka、Manami Kishi、Takao Tanahashi、Hiromi Yoshida、Chiaki Okuda、Yoshiyuki Mizushina

  DOI：10.1248/cpb.57.476

  日期：——

  trans- and cis-Icosyl, docosyl, and tetracosyl p-coumarates, constituents of Artemisia annua L., and their structurally-related compounds were synthesized and evaluated for inhibitory activity on DNA polymerases alpha and beta. Among 30 compounds synthesized, octadecyl trans- and cis-p-coumarates and octadecyl p-hydroxyphenylpropiolate showed strong inhibitory activity on DNA polymerases alpha and

  合成了Artemisia annua L.的组成部分的反式和顺式-二十烷基，二十二烷基和十四烷基对-香豆酸酯及其结构相关的化合物，并评估了它们对DNA聚合酶α和β的抑制活性。在合成的30种化合物中，十八烷基反式和顺式对-香豆酸酯和十八烷基对羟基苯丙酸酯显示出对DNA聚合酶α和β的强抑制活性。
• 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
• Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold
  作者：Razieh Hosseini、Fatemeh Moosavi、Hamid Rajaian、Tiago Silva、Diogo Magalhães e Silva、Pedro Soares、Luciano Saso、Najmeh Edraki、Ramin Miri、Fernanda Borges、Omidreza Firuzi

  DOI：10.1111/cbdd.12829

  日期：2016.12

  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.