caffeic acid ethylene ester

• 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: caffeic acid ethylene ester
• 英文别名: 2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxyethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: LTACDIIPISHXNX-FCXRPNKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (E)-3,4-di-O-acetylcaffeoyl chloride 在 吡啶 、 盐酸 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 3.0h， 生成 caffeic acid ethylene ester
  参考文献：
  名称：

  Chicoric Acid Analogues as HIV-1 Integrase Inhibitors

  摘要：

  The present study was undertaken to examine structural features of L-chicoric acid (3) which are important for potency against purified HIV-1 integrase and for reported cytoprotective effects in cell-based systems. Through a progressive series of analogues, it was shown that enantiomeric D-chicoric acid (4) retains inhibitory potency against purified integrase equal to its L-counterpart and further that removal of either one or both carboxylic functionalities results in essentially no loss of inhibitory potency. Additionally, while two caffeoyl moieties are required, attachment of caffeoyl groups to the central linking structure can be achieved via amide or mixed amide/ester linkages. More remarkable is the finding that blockage of the catechol functionality through conversion to tetraacetate esters results in almost no loss of potency, contingent on the presence of at least one carboxyl group on the central linker. Taken as a whole, the work has resulted in the identification of new integrase inhibitors which may be regarded as bis-caffeoyl derivatives of glycidic acid and amino acids such as serine and beta-aminoalanine. The present study also examined the reported ability of chicoric acid to exert cytoprotective effects in HIV-infected cells. It was demonstrated in target and cell-based assays that the chicoric acids do not significantly inhibit other targets associated with HIV-1 replication, including reverse transcription, protease function, NCp7 zinc finger function, or replication of virus from latently infected cells. In CEM cells, for both the parent chicoric acid and selected analogues, antiviral activity was observable under specific assay conditions and with high dependence on the multiplicity of viral infection. However, against HIV-1- and HIV-2-infected MT-4 cells, the chicoric acids and their tetraacetylated esters exhibited antiviral activity (50% effective concentration (EC(50)) ranging from 1.7 to 20 mu M and 50% inhibitory concentration (IC(50)) ranging from 40 to 60 mu M).

  DOI：

  10.1021/jm980531m

文献信息

• Synthesis and Evaluation of Antioxidant Activities of Novel Hydroxyalkyl Esters and Bis-Aryl Esters Based on Sinapic and Caffeic Acids
  作者：Oscar Laguna、Erwann Durand、Bruno Baréa、Sylvie Dauguet、Frédéric Fine、Pierre Villeneuve、Jérôme Lecomte

  DOI：10.1021/acs.jafc.0c03711

  日期：2020.9.2

  steric hindrance in hydroxyalkyl esters, and intramolecular interactions in bis-aryl esters. Regarding the two bis-aryl esters series in emulsion, the antioxidant capacity was improved with alkyl chain lengthening up to four carbons, after which it decreased for longer chains. This “cutoff” effect was not observed for both hydroxyalkyl esters series for which the alkyl chain lengthening results in a decrease

  由芥子酸和咖啡酸以及链长从2至12个碳原子增加的脂肪族α，ω-二醇合成了新型羟烷基酯和双芳基酯。然后，评估它们在模型水包油乳液中的抗自由基反应性（DPPH测定）和抗氧化活性（CAT测定）。与相应的酚酸相比，所有酯均显示出较低的抗自由基活性。这种减少与羟烷基酯的空间位阻以及双芳基酯的分子内相互作用有关。关于乳液中的两个双芳基酯系列，随着烷基链延长至四个碳原子，抗氧化剂的能力得到了提高，此后对于更长的链，抗氧化剂的能力下降。
• [EN] ACETYLATED AND RELATED ANALOGUES OF CHICORIC ACID AS HIV INTEGRASE INHIBITORS<br/>[FR] ANALOGUES ACETYLES ET CORRESPONDANTS D'ACIDE CHICORIQUE EN TANT QU'INHIBITEURS DE L'INTEGRASE DU VIH
  申请人：US HEALTH

  公开号：WO2000063152A1

  公开（公告）日：2000-10-26

  Chicoric acid analogues and derivatives have activity against HIV-1 integrase. The structural features that are required for this activity are elucidated by assaying these analogues and derivatives against HIV-1 integrase. Furthermore, methods of synthesis of the enantiomers of chicoric acid itself, as well as its analogues and derivatives, are disclosed. Additionally, methods of use of chicoric acid analogues and derivatives to inhibit HIV-1 integrase are disclosed, as are compositions comprising chicoric acid analogues and derivatives.

  Chicoric酸类似物和衍生物具有抗HIV-1整合酶的活性。通过对这些类似物和衍生物对HIV-1整合酶的测定，阐明了实现这种活性所需的结构特征。此外，还公开了合成Chicoric酸本身及其类似物和衍生物的对映体的方法。此外，还公开了使用Chicoric酸类似物和衍生物抑制HIV-1整合酶的方法，以及包含Chicoric酸类似物和衍生物的组合物。
• STEVIOL GLYCOSIDE SOLUBILITY ENHANCERS
  申请人：CARGILL, INCORPORATED

  公开号：US20190223481A1

  公开（公告）日：2019-07-25

  A solubilized steviol glycoside composition including one or more steviol glycosides and one or more steviol glycoside solubility enhancers can be used as a sweetener composition to sweeten other compositions (sweetenable compositions) such as foods, beverages, medicines, oral hygiene compositions, pharmaceuticals, nutraceuticals, and the like.
• STEVIOL GLYCOSIDE COMPOSITIONS WITH REDUCED SURFACE TENSION
  申请人：CARGILL, INCORPORATED

  公开号：US20190223482A1

  公开（公告）日：2019-07-25

  A steviol glycoside composition with reduced surface tension. The reduced surface tension steviol glycoside composition includes an aqueous solution of a steviol glycoside and a surface tension reducing compound in an amount effective to reduce surface tension. Method for reducing surface tension in a steviol glycoside solution includes contacting a steviol glycoside and a surface tension reducing compound.
• SENSORY MODIFIER COMPOUNDS
  申请人：CARGILL, INCORPORATED

  公开号：US20190223483A1

  公开（公告）日：2019-07-25

  A steviol glycoside composition having modified sensory attributes including reduced sweetness linger and/or increased sweetness intensity. The steviol glycoside composition comprises a steviol glycoside and a sensory modifier compound in an amount effective to modify the sensory attributes of the steviol glycoside.