trans-decyl 3-(3,4-dihydroxyphenyl)propenoate

• 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: trans-decyl 3-(3,4-dihydroxyphenyl)propenoate
• 英文别名: (E)-decyl 3-(3,4-dihydroxyphenyl)acrylate；3,4-dihydroxycinnamic acid n-decyl ester；3,4-dihydroxycinnamic acid decyl ester；caffeic acid decyl ester；n-decanyl caffeate；decyl caffeate；Decyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: INKXBBFEJTVQBM-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 trans-decyl 3-(3,4-dihydroxyphenyl)propenoate
  参考文献：
  名称：

  Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line

  摘要：

  Caffeic acid phenethyl ester (CAPE, 2) and its twenty analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02 muM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10 mug/mL towards murine colon 26-L5 carcinoma cells. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00138-4

文献信息

• [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。
• Fine-tuning of the hydrophobicity of caffeic acid: studies on the antimicrobial activity against Staphylococcus aureus and Escherichia coli
  作者：Mafalda Andrade、Sofia Benfeito、Pedro Soares、Diogo Magalhães e Silva、Joana Loureiro、Anabela Borges、Fernanda Borges、Manuel Simões

  DOI：10.1039/c5ra05840f

  日期：——

  widely recognized. Some phytochemical products, produced by plants as part of their chemical defense strategies, are regarded as new stimulii to develop novel antimicrobials that are not as vulnerable as current drugs to bacterial resistance mechanisms. In this study, the antimicrobial activity and mode of action of caffeic acid (CAF) and a series of CAF alkyl esters was assessed against Escherichia coli

  由于不适当使用和过度使用抗菌素引起的细菌对多种药物的耐药性增加是全球关注的问题。为了避免这个问题，人们广泛认可了对开发新的活性剂的追求。植物产生的一些植物化学产品是其化学防御策略的一部分，被认为是开发新型抗微生物剂的新刺激，这些抗微生物剂不像目前的药物那样容易受到细菌耐药性机制的影响。在这项研究中，评估了咖啡酸（CAF）和一系列CAF烷基酯的抗微生物活性和作用方式对大肠杆菌和金黄色葡萄球菌的作用，目的是分析烷基酯侧链长度对活性的影响。最小抑菌浓度（MIC），最小杀菌浓度（MBC），理化表面性质的变化和细胞内钾泄漏被用作抗菌作用方式的生理指标。发现CAF烷基酯是对两种细菌有效的抗微生物剂。它们的活性直接取决于它们的亲脂性，亲脂性影响细菌的敏感性，细菌的理化性质和膜的完整性。大肠杆菌不如金黄色葡萄球菌易感对化合物的作用。较长的烷基侧链对革兰氏阳性细菌更有效，而中等长度的烷基侧链化合物对革兰氏阴
• 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.
• Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages
  作者：Koji Uwai、Yuu Osanai、Takuma Imaizumi、Syu-ichi Kanno、Mitsuhiro Takeshita、Masaaki Ishikawa

  DOI：10.1016/j.bmc.2008.07.006

  日期：2008.8

  Caffeic acid esters, one of the components of propolis, are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities. Although, the anti-inflammatory activities of caffeic acid esters have been studied by analyzing their structure, the detailed mechanisms of their activities remain unclear. Thus, in this study, we examined the function of the ester functional group and the alkyl side chain (alcoholic part) and transformed caffeic acid to several derivatives. The inhibitory effect of these derivatives on NO production in murine macrophage RAW264.7 cells was dependent on the length and size of the alkyl moiety, and undecyl caffeate was the most potent inhibitor of NO production. In addition, individual experiments using undecanol, caffeic acid, undecanol plus caffeic acid, and undecyl caffeate showed that the connection between caffeic acid and the alkyl chain is critical for activity. Amide and ketone derivatives showed that not only the ester functional group but also the amide and ketone functional groups exhibit an inhibitory effect on NO production. (c) 2008 Elsevier Ltd. All rights reserved.