benzyl 3-(3,4-dihydroxyphenyl)propanoate

• 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: benzyl 3-(3,4-dihydroxyphenyl)propanoate
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: NPPXMKKJYNRZBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3,4-二羟基苯基丙酸 在 咪唑 、 盐酸 、 氯化亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 77.5h， 生成 benzyl 3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD

  摘要：

  A new strategy for treating Pseudomonas aeruginosa infections could be disrupting the Pseudomonas Quinolone Signal (PQS) quorum sensing (QS) system. The goal is to impair communication among the cells and, hence, reduce the expression of virulence factors and the formation of biofilms. PqsD is an essential enzyme for the synthesis of PQS and shares some features with chalcone synthase (CHS2), an enzyme expressed in Medicago sativa. Both proteins are quite similar concerning the size of the active site, the catalytic residues and the electrostatic surface potential at the entrance of the substrate tunnel. Hence, we evaluated selected substrates of the vegetable enzyme as potential inhibitors of the bacterial protein. This similarity-guided approach led to the identification of a new class of PqsD inhibitors having a catechol structure as an essential feature for activity, a saturated linker with two or more carbons and an ester moiety bearing bulky substituents. The developed compounds showed PqsD inhibition with IC50 values in the single-digit micromolar range. The binding mode of these compounds was investigated by Surface Plasmon Resonance (SPR) experiments revealing that their interaction with the protein is not influenced by the presence of the anthranilic acid bound to active site cysteine. Importantly, some compounds reduced the signal molecule production in cellulo. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.055

文献信息

• CATECHOL-BASED DERIVATIVES FOR TREATING OR PREVENTING DIABETICS
  申请人：Kuo Yueh-Hsiung

  公开号：US20090143397A1

  公开（公告）日：2009-06-04

  The present invention provides a catechol-based derivative and a pharmaceutical acceptable salt therefrom and a solvate therefrom. A pharmaceutical composition for preventing or treating diabetics and ischemics, comprising a catechol-based derivative of formula (I) and at least one selected from the group consisting of a pharmaceutical excipient, a diluent and a carrier.

  本发明提供了一种基于邻苯二酚的衍生物及其药用可接受的盐和溶剂化合物。一种用于预防或治疗糖尿病和缺血症的药物组合物，包括具有化学式(I)的基于邻苯二酚的衍生物和来自药用辅料、稀释剂和载体中选择的至少一种成分。
• Mechanism of toxicity of esters of Caffeic and dihydrocaffeic acids
  作者：Beth Etzenhouser、Corwin Hansch、Sanjay Kapur、C.Dias Selassie

  DOI：10.1016/s0968-0896(00)00238-8

  日期：2001.1

  Ten esters each of caffeic acid and dihydrocaffeic acid have recently been synthesized. Cytotoxicity evaluations of these esters versus L1210 leukemia and MCF-7 breast cancer cells in culture have led to the delineation of substantially different QSAR for each series. The L1210 QSAR for dihydrocaffeic acid esters resembles the QSAR obtained for simple phenols and estrogenic phenols. However, the QSAR

  最近已合成了咖啡酸和二氢咖啡酸的十种酯。这些酯对培养中的L1210白血病和MCF-7乳腺癌细胞的细胞毒性评估已导致每个系列的QSAR均存在明显差异。二氢咖啡因酸酯的L1210 QSAR与简单酚和雌激素酚获得的QSAR相似。但是，与咖啡酸酯有关的QSAR与它的姊妹QSAR有很大不同。该差异可以归因于侧链中烯烃键的存在。咖啡酸的辛酯对白血病细胞的毒性是广泛研究的苯乙酯CAPE的十倍。
• US8088818B2
  申请人：——

  公开号：US8088818B2

  公开（公告）日：2012-01-03