3-phenylpropyl 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: 3-phenylpropyl 3-(3,4-dihydroxyphenyl)propanoate
• 英文别名: 3-phenylpropyl-3-(3,4-dihydroxyphenyl)propanoate
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: HSOZWRWDCRLWFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  (E)-3-(3,4-bis(methoxymethoxy)phenyl)acrylic acid 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 3-phenylpropyl 3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441

文献信息

• Synthesis and Antiradical/Antioxidant Activities of Caffeic Acid Phenethyl Ester and Its Related Propionic, Acetic, and Benzoic Acid Analoguesc
  作者：Luc LeBlanc、Aurélie Paré、Jacques Jean-François、Martin Hébert、Marc Surette、Mohamed Touaibia

  DOI：10.3390/molecules171214637

  日期：——

  Caffeic acid phenethyl ester (CAPE) is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl) propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl)

  咖啡酸苯乙酯 (CAPE) 是一种从蜂胶中分离出来的生物活性成分。合成了一系列 CAPE 类似物并分析了它们的抗自由基/抗氧化作用。双键和共轭体系的存在对抗氧化作用的影响用从3-(3,4-二羟基苯基)丙酸获得的类似物进行评价。那些从 2-(3,4-二羟基苯基) 乙酸和 3,4-二羟基苯甲酸获得的物质可以评估羰基和芳族体系之间存在两个碳的影响。
• 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。
• 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.
• Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues
  作者：Li Hong Hu、Hong Bin Zou、Jing Xu Gong、Hai Bo Li、Lei Xiang Yang、Wei Cheng、Chang Xin Zhou、Hua Bai、Françoise Guéritte、Yu Zhao

  DOI：10.1021/np0496441

  日期：2005.3.1

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.