diethyl <<2-(benzyloxy)anilino>methylene>malonate | 26774-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl <<2-(benzyloxy)anilino>methylene>malonate
• 英文别名: o-Benzyloxyanilino-methylenmalonsaeure-diaethylester；Diethyl 2-[(2-phenylmethoxyanilino)methylidene]propanedioate
• CAS: 26774-07-2
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: QERXVLHFLJDYRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl <<2-(benzyloxy)anilino>methylene>malonate 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 0.75h， 生成 ethyl 8-(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
• 作为产物：
  描述：

  2-苄氧基苯胺 、 乙氧基甲叉丙二酸二乙酯 反应 2.0h， 以90%的产率得到diethyl <<2-(benzyloxy)anilino>methylene>malonate
  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

• 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.