ethyl 7-(benzyloxy)-4-chloroquinolone-3-carboxylate | 19501-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 7-(benzyloxy)-4-chloroquinolone-3-carboxylate
• 英文别名: Ethyl 4-chloro-7-phenylmethoxyquinoline-3-carboxylate
• CAS: 19501-17-8
• 化学式: C₁₉H₁₆ClNO₃
• 分子量: 341.794
• InChiKey: PSQAGMWTECXBAL-UHFFFAOYSA-N

物化性质

• 沸点：
  469.7±40.0 °C(predicted)
• 密度：
  1.276±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 7-(benzyloxy)-4-chloroquinolone-3-carboxylate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以86.4 %的产率得到(7-(benzyloxy)-4-chloroquinolin-3-yl)methanol
  参考文献：
  名称：

  CN116574054

  摘要：

  公开号：
• 作为产物：
  描述：

  3-苄氧基苯胺 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 2.75h， 生成 ethyl 7-(benzyloxy)-4-chloroquinolone-3-carboxylate
  参考文献：
  名称：

  Computer-Aided Molecular Modeling, Synthesis, and Biological Evaluation of 8-(Benzyloxy)-2-phenylpyrazolo[4,3-c]quinoline as a Novel Benzodiazepine Receptor Agonist Ligand

  摘要：

  Using computer-aided conformational analysis, based on molecular dynamics simulation, cluster analysis, and Monte Carlo techniques, we have designed and synthesized compounds in which a benzyloxy substituent has been incorporated into a series of pyrazoloquinoline benzodiazepine receptor (BZR) ligands, Earlier studies had shown that the benzyloxy group could act as part of the agonist pharmacophoric determinant in the beta-carboline ring system. Furthermore, the agonist beta-carboline had been correlated with a binding site orientation and volume fit for an agonist 6-phenylimidazobenzodiazepine carboxylate. The present study was undertaken to determine whether the benzyloxy substituent could be used as an agonist pharmacophoric descriptor for the phenylpyrazolo[4,3-c]quinolin-3-one BZR ligands, The results of a determination of GABA shift ratios for the synthetic ligands indicate that 8-(benzyloxy)-2-phenylpyrazolo[4,3-c]quinolin-3-one can be predicted to be an agonist at the BZR.

  DOI：

  10.1021/jm00006a014

文献信息

• 10.1016/j.ejmech.2024.116534
  作者：Lu, Yunlong、Liang, Zhenlin、Liu, Lijuan、Zhou, Yanyu、Liu, Chao、Zhao, Zhihao、Zheng, Tianpeng、Du, Qianming、Liu, Wukun

  DOI：10.1016/j.ejmech.2024.116534

  日期：——

  approach for estrogen receptor (ER)-positive breast cancer. Currently, cyclin-dependent kinase 4/6 (CDK4/6) inhibitors are combined with aromatase inhibitors (AIs) or selective estrogen receptor degraders (SERDs) as first-line therapy for advanced ER-positive breast cancer. Herein, a new family of quinoline scaffold SERDs was synthesized and evaluated in MCF-7 cells. Among them, compounds and exhibited

  联合疗法被证明是治疗雌激素受体（ER）阳性乳腺癌的有效方法。目前，细胞周期蛋白依赖性激酶4/6（CDK4/6）抑制剂与芳香酶抑制剂（AI）或选择性雌激素受体降解剂（SERD）联合作为晚期ER阳性乳腺癌的一线治疗。在此，合成了一个新的喹啉支架 SERD 家族，并在 MCF-7 细胞中进行了评估。其中，化合物 和 单独使用以及与 ribociclib（CDK4/6 抑制剂）联合使用均表现出显着的 MCF-7 抑制作用。同时，化合物可有效降解ER并抑制ER下游信号通路。有趣的是，化合物和 MCF-7 细胞中的损伤相关分子模式 (DAMP) 诱导内质网应激 (ERS) 并引发免疫原性细胞死亡 (ICD)。这些发现强调了口服 SERD 在 ER 阳性乳腺癌治疗中的免疫相关和增强的抗增殖作用。
• Computer-Aided Molecular Modeling, Synthesis, and Biological Evaluation of 8-(Benzyloxy)-2-phenylpyrazolo[4,3-c]quinoline as a Novel Benzodiazepine Receptor Agonist Ligand
  作者：C. G. Wang、T. Langer、P. G. Kamath、Z.-Q. Gu、P. Skolnick、R. Ian Fryer

  DOI：10.1021/jm00006a014

  日期：1995.3

  Using computer-aided conformational analysis, based on molecular dynamics simulation, cluster analysis, and Monte Carlo techniques, we have designed and synthesized compounds in which a benzyloxy substituent has been incorporated into a series of pyrazoloquinoline benzodiazepine receptor (BZR) ligands, Earlier studies had shown that the benzyloxy group could act as part of the agonist pharmacophoric determinant in the beta-carboline ring system. Furthermore, the agonist beta-carboline had been correlated with a binding site orientation and volume fit for an agonist 6-phenylimidazobenzodiazepine carboxylate. The present study was undertaken to determine whether the benzyloxy substituent could be used as an agonist pharmacophoric descriptor for the phenylpyrazolo[4,3-c]quinolin-3-one BZR ligands, The results of a determination of GABA shift ratios for the synthetic ligands indicate that 8-(benzyloxy)-2-phenylpyrazolo[4,3-c]quinolin-3-one can be predicted to be an agonist at the BZR.
• CN116574054
  申请人：——

  公开号：——

  公开（公告）日：——