2-phenylethyl 3,4,5-trihydroxybenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenylethyl 3,4,5-trihydroxybenzoate
• 英文别名: phenethyl 3,4,5-trihydroxybenzoate；2-phenylethan-1-yl gallate
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: UHPALUGVFOSLRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,5-三苄氧基苯甲酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-phenylethyl 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  Differential Inhibition of polymerase and Strand-Transfer Activities of HIV-1 Reverse Transcriptase

  摘要：

  A new class of inhibitors of HIV-1 reverse transcriptase obtained by the systematic structural simplification of epicatechin and epigallocatechin gallates are also shown here to inhibit DNA-strand-transfer, a process critical to the completion of the HIV-1-RT reproduction and to recombination-associated mutation of the virus. Up to 80-fold selectivity for DNA-strand-transfer inhibition over polymerase inhibition was observed for a defined subset of these agents. Such specific DNA-strand-transfer inhibitors may have important therapeutic potential. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00827-7

文献信息

• Catechol-based inhibitors of bacterial urease
  作者：Aikaterini Pagoni、Theohari Daliani、Katarzyna Macegoniuk、Stamatia Vassiliou、Łukasz Berlicki

  DOI：10.1016/j.bmcl.2019.02.032

  日期：2019.5

  structure. Forty amide and ester derivatives of 3,4-dihydroxyphenylacetic acid, caffeic acid, ferulic acid and gallic acid were obtained and screened against Sporosarcinia pasteurii urease. The most active compound, namely propargyl ester of 3,4-dihydroxyphenylacetic acid exhibited IC50 = 518 nM andkinact/Ki = 1379 M-1 s-1. Inhibitory activity of this compound was better and toxicity lower than those obtained

  基于儿茶酚结构开发了靶向的脲酶共价抑制剂。获得了40种3，4-二羟基苯基乙酸，咖啡酸，阿魏酸和没食子酸的酰胺和酯衍生物，并针对巴氏芽孢杆菌巴氏脲酶进行了筛选。活性最高的化合物，即3,4-二羟基苯基乙酸的炔丙基酯显示IC50 = 518 nM，运动/ Ki = 1379 M-1 s-1。与起始化合物邻苯二酚相比，该化合物的抑制活性更好，毒性更低。分子建模研究揭示了一种结合结构-活性关系的结合方式。
• Phenethyl Ester of Gallic Acid Ameliorates Experimental Autoimmune Encephalomyelitis
  作者：Goran Stegnjaić、Antonios D. Tsiailanis、Milica Lazarević、Vasileios K. Gkalpinos、Neda Djedovic、Thomas Antoniou、Suzana Stanisavljević、Mirjana Dimitrijević、Miljana Momčilović、Đorđe Miljković、Andreas G. Tzakos、Bojan Jevtić

  DOI：10.3390/molecules27248770

  日期：——

  Gallic acid is a phenolic acid present in various plants, nuts, and fruits. It is well known for its anti-oxidative and anti-inflammatory properties. The phenethyl ester of gallic acid (PEGA) was synthesized with the aim of increasing the bioavailability of gallic acid, and thus its pharmacological potential. Here, the effects of PEGA on encephalitogenic cells were examined, and PEGA was found to modulate the inflammatory activities of T cells and macrophages/microglia. Specifically, PEGA reduced the release of interleukin (IL)-17 and interferon (IFN)-γ from T cells, as well as NO, and IL-6 from macrophages/microglia. Importantly, PEGA ameliorated experimental autoimmune encephalomyelitis, an animal model of chronic inflammatory disease of the central nervous system (CNS)—multiple sclerosis. Thus, PEGA is a potent anti-inflammatory compound with a perspective to be further explored in the context of CNS autoimmunity and other chronic inflammatory disorders.

  没食子酸是一种酚酸，存在于各种植物、坚果和水果中。它因具有抗氧化和抗炎特性而闻名。合成没食子酸苯乙酯（PEGA）的目的是提高没食子酸的生物利用率，从而提高其药理潜力。在这里，我们研究了 PEGA 对致脑细胞的影响，发现 PEGA 可以调节 T 细胞和巨噬细胞/小胶质细胞的炎症活动。具体来说，PEGA 可减少 T 细胞释放的白细胞介素 (IL)-17 和干扰素 (IFN)-γ，以及巨噬细胞/小胶质细胞释放的 NO 和 IL-6。重要的是，PEGA 可改善实验性自身免疫性脑脊髓炎（一种中枢神经系统（CNS）慢性炎症性疾病--多发性硬化症的动物模型）。因此，PEGA 是一种强效抗炎化合物，有望在中枢神经系统自身免疫和其他慢性炎症性疾病方面得到进一步探索。
• MODULATORS OF LIPOXYGENASE AND CYCLOOXYGENASE ENZYME ACTIVITY
  申请人：Universite de Moncton

  公开号：US20190119194A1

  公开（公告）日：2019-04-25

  The present invention relates to modulators of lipoxygenase and/or cyclooxygenase enzyme. The present invention also provides compositions comprising such modulators, and methods therewith for treating lipoxygenase receptor mediated diseases.
• US4418037A
  申请人：——

  公开号：US4418037A

  公开（公告）日：1983-11-29
• US5084593A
  申请人：——

  公开号：US5084593A

  公开（公告）日：1992-01-28