(E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl)acrylate
• 英文别名: methyl (E)-2-(7-chloroquinolin-4-yl)sulfanyl-3-(4-hydroxyphenyl)prop-2-enoate
• 化学式: C₁₉H₁₄ClNO₃S
• 分子量: 371.844
• InChiKey: RZJMJCGMRASOSP-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl)acrylate 、 藜芦酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以35%的产率得到4-[(E)-2-(methoxycarbonyl)-2-(7-chloroquinolin-4-ylthio)vinyl]phenyl 3,4-dimethoxybenzoate
  参考文献：
  名称：

  （E）-丙烯酸2-（7-氯喹啉-4-基硫基）-3-（4-羟苯基）甲酯的抗疟和抗癌活性的优化

  摘要：

  生物活性物质的化学修饰形式特别适用于克服与药物配方，药物输送和不良的药代动力学特性相关的障碍。在这项研究中，通过使用一步法从先前描述的1合成合成了一系列14种（E）-甲基2-（7-氯喹啉-4-基硫基）-3-（4-羟基苯基）丙烯酸酯（2-15）被我们视为潜在的抗疟和抗肿瘤药物。分子被评估为β-血凝素形成的抑制剂，其中大多数显示出显着的抑制值（％> 70）。最好的抑制剂在体内测试为潜在感染疟疾的小鼠，感染了对苯醌敏感的氯喹敏感菌株。其中三个（5、6和15）显示出与氯喹相当的抗疟活性。还，评价了这些分子对两种人类癌细胞系（Jurkat E6.1和HL60）的细胞毒性活性以及人类淋巴细胞的原代培养。除类似物2-6、8和10-12外，大多数合成化合物对癌细胞系均显示出细胞毒性，而不会影响正常细胞。该化合物的效价为15×1，且14> 7、9和13。流式细胞仪分析表明24小时后凋亡细胞死亡增加。该化合物

  DOI：

  10.1016/j.bmc.2017.12.022
• 作为产物：
  描述：

  methyl 2-(7-chloroquinolin-4-ylthio)acetate 、 对羟基苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 以75%的产率得到(E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl)acrylate
  参考文献：
  名称：

  Potential antitumour and pro-oxidative effects of (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl) acrylate (QNACR)

  摘要：

  Context: Characterization of the pro-oxidant activity of QNACR.Objectives: Reactive oxygen species (ROS) induce cellular damage and represent unique opportunities to kill malignant cells. In this study, we synthesized and evaluated the new compound, (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl) acrylate (QNACR) as potential pro-oxidative agent against breast cancer.Methods: Oxidative stress biomarkers such as ROS, thiobarbuturic acid reactive species (TBARs) and different antioxidant enzyme activities were determined in cell lysates.Results: QNACR showed cytotoxic and more selective effects to tumour MCF7 cells (IC50 < 25 mu M) compared to antitumour controls, inducing ROS and TBARs parallel to inhibitions of catalase (CAT), glucose-6-phosphate dehydrogenase (G6PDH) and 6-phosphogluconate dehydrogenase (6PGDH). Longer exposures to QNACR triggered adaptive effects increasing the overall activities of CAT, glutathione reductase, G6PDH and 6PGDH, but eventually the adaptation changes faded and cells died.Conclusion: QNACR led to remarkable modifications in the oxidative status of tumour cells, proposing this compound as potential alternative for antitumour therapy.

  DOI：

  10.3109/14756366.2012.736385

文献信息

• Optimization of antimalarial, and anticancer activities of (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl) acrylate
  作者：Jesús A. Romero、María E. Acosta、Neira D. Gamboa、Michael R. Mijares、Juan B. De Sanctis、Jaime E. Charris

  DOI：10.1016/j.bmc.2017.12.022

  日期：2018.2

  susceptible strain. Three of them (5, 6, and 15) displayed antimalarial activity comparable to that of chloroquine. Also, molecules were evaluated for their cytotoxic activity against two human cancer cell lines (Jurkat E6.1 and HL60) and primary culture of human lymphocytes. Most of the synthesized compounds, except for analogs 2-6, 8, and 10-12, displayed cytotoxicity against cancer cell lines without

  生物活性物质的化学修饰形式特别适用于克服与药物配方，药物输送和不良的药代动力学特性相关的障碍。在这项研究中，通过使用一步法从先前描述的1合成合成了一系列14种（E）-甲基2-（7-氯喹啉-4-基硫基）-3-（4-羟基苯基）丙烯酸酯（2-15）被我们视为潜在的抗疟和抗肿瘤药物。分子被评估为β-血凝素形成的抑制剂，其中大多数显示出显着的抑制值（％> 70）。最好的抑制剂在体内测试为潜在感染疟疾的小鼠，感染了对苯醌敏感的氯喹敏感菌株。其中三个（5、6和15）显示出与氯喹相当的抗疟活性。还，评价了这些分子对两种人类癌细胞系（Jurkat E6.1和HL60）的细胞毒性活性以及人类淋巴细胞的原代培养。除类似物2-6、8和10-12外，大多数合成化合物对癌细胞系均显示出细胞毒性，而不会影响正常细胞。该化合物的效价为15×1，且14> 7、9和13。流式细胞仪分析表明24小时后凋亡细胞死亡增加。该化合物
• Potential antitumour and pro-oxidative effects of (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl) acrylate (QNACR)
  作者：Juan R. Rodrigues、Rosa Ferrer、Neira Gamboa、Jaime Charris、Fernando Antunes

  DOI：10.3109/14756366.2012.736385

  日期：2013.12.1

  Context: Characterization of the pro-oxidant activity of QNACR.Objectives: Reactive oxygen species (ROS) induce cellular damage and represent unique opportunities to kill malignant cells. In this study, we synthesized and evaluated the new compound, (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl) acrylate (QNACR) as potential pro-oxidative agent against breast cancer.Methods: Oxidative stress biomarkers such as ROS, thiobarbuturic acid reactive species (TBARs) and different antioxidant enzyme activities were determined in cell lysates.Results: QNACR showed cytotoxic and more selective effects to tumour MCF7 cells (IC50 < 25 mu M) compared to antitumour controls, inducing ROS and TBARs parallel to inhibitions of catalase (CAT), glucose-6-phosphate dehydrogenase (G6PDH) and 6-phosphogluconate dehydrogenase (6PGDH). Longer exposures to QNACR triggered adaptive effects increasing the overall activities of CAT, glutathione reductase, G6PDH and 6PGDH, but eventually the adaptation changes faded and cells died.Conclusion: QNACR led to remarkable modifications in the oxidative status of tumour cells, proposing this compound as potential alternative for antitumour therapy.