isopropyl 3-(3,4-dihydroxyphenyl)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: isopropyl 3-(3,4-dihydroxyphenyl)propanoate
• 英文别名: L 159,084；Propan-2-yl 3-(3,4-dihydroxyphenyl)propanoate；propan-2-yl 3-(3,4-dihydroxyphenyl)propanoate
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: HDZYZILZFWKXGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  3,4-二羟基苯甲醛 在 硫酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.5h， 生成 isopropyl 3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  一种适用于抗病毒并具有抗炎作用的化合物及其制备方法与应用

  摘要：

  本发明涉及生物医药研发领域，具体涉及一种适用于抗病毒并具有抗炎作用的化合物及其制备方法与应用。本发明化合物的结构如下式A所示，其中每个变量如本文所定义。本发明通过对结构优化和构效关系研究，首次发现：本发明所发现和提供的化合物是SARS‑CoV‑23CL蛋白酶的共价抑制剂，是活性更强的3CL蛋白酶抑制剂并具有抗炎作用。#imgabs0#

  公开号：

  CN118580146A

文献信息

• 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。
• Design, synthesis and biological evaluation of small molecular polyphenols as entry inhibitors against H5N1
  作者：Jian Yang、Jing Xiang Yang、Fang Zhang、Gang Chen、Wei Pan、Rui Yu、Shuwen Wu、Po Tien

  DOI：10.1016/j.bmcl.2014.04.057

  日期：2014.6

  To find novel compounds against H5N1, three series of known or novel small molecular polyphenols were synthesized and tested in vitro for anti-H5N1 activity. In addition, the preliminary structure-antiviral activity relationships were elaborated. The results showed that some small molecular polyphenols had better anti-H5N1 activity, and could serve as novel virus entry inhibitors against H5N1, likely targeting to HA2 protein. Noticeably, compound 4a showed the strongest activity against H5N1 among these compounds, and the molecular modeling analysis also suggested that this compound might target to HA2 protein. Therefore, compound 4a is well qualified to serve as a lead compound or scaffold for the further development of H5N1 entry inhibitor. (C) 2014 Elsevier Ltd. All rights reserved.
• Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD
  作者：Giuseppe Allegretta、Elisabeth Weidel、Martin Empting、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2014.11.055

  日期：2015.1

  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.