3-(3,4-dihydroxyphenyl)propanoic acid butyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(3,4-dihydroxyphenyl)propanoic acid butyl ester
• 英文别名: Butyl 3-(3,4-dihydroxyphenyl)propanoate
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: FTTPHDMAQAAUAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  对羟基苯丙酸 在 三甲基氯硅烷 、 Agaricus bisporus 、 氧气 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 3-(3,4-dihydroxyphenyl)propanoic acid butyl ester
  参考文献：
  名称：

  Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity

  摘要：

  Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.026

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。
• Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate
  作者：Bartłomiej Zieniuk、Chimaobi James Ononamadu、Karina Jasińska、Katarzyna Wierzchowska、Agata Fabiszewska

  DOI：10.3390/molecules27155024

  日期：——

  aqueous environments, the processes of the ester bond formations are encountered in organic solvents. The aim of the current research was to carry out the lipase-catalyzed synthesis of an ester of dihydrocaffeic acid. The synthesized compound was then evaluated for antioxidant and antimicrobial activities. However, the vast majority of its antioxidant activity was retained, which was demonstrated by means

  绿色化学方法，例如脂肪酶催化的酯化，是获得有价值的化合物的有前途的方法。在使用脂肪酶的情况下，与水环境不同，酯键的形成过程是在有机溶剂中遇到的。目前研究的目的是进行脂肪酶催化的二氢咖啡酸酯的合成。然后评估合成的化合物的抗氧化和抗微生物活性。然而，其大部分抗氧化活性得以保留，这通过DPPH·（2,2-二苯基-1-苦基肼）和CUPRAC（铜离子降低抗氧化能力）方法得到证明。关于其抗菌特性，对米根霉的抗真菌活性值得一提。最低抑菌浓度和杀真菌浓度分别为 1 和 2 mM。高抗真菌活性促使使用分子对接研究来验证二氢咖啡酸丁酯的潜在蛋白质靶标。对于一种真菌蛋白，即 14-α 甾醇脱甲基酶 B，观察到该酯与三唑类药物艾沙康唑具有相当的结合能，但相互作用的氨基酸残基不同。
• Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity
  作者：Tiziana Bozzini、Giorgia Botta、Michela Delfino、Silvano Onofri、Raffaele Saladino、Donatella Amatore、Rossella Sgarbanti、Lucia Nencioni、Anna Teresa Palamara

  DOI：10.1016/j.bmc.2013.10.026

  日期：2013.12

  Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties. (C) 2013 Elsevier Ltd. All rights reserved.
• Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses
  作者：Giorgia Botta、Bruno Mattia Bizzarri、Adriana Garozzo、Rossella Timpanaro、Benedetta Bisignano、Donatella Amatore、Anna Teresa Palamara、Lucia Nencioni、Raffaele Saladino

  DOI：10.1016/j.bmc.2015.07.061

  日期：2015.9

  Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection. (C) 2015 Elsevier Ltd. All rights reserved.