ethyl methyl 4-oxo-6-(pentafluoroethyl)-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate | 114184-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl methyl 4-oxo-6-(pentafluoroethyl)-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate
• 英文别名: ethyl methyl 4-oxo-6-(pentafluoroethyl)-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate；2-O-ethyl 8-O-methyl 4-oxo-6-(1,1,2,2,2-pentafluoroethyl)-10-propylpyrano[3,2-g]quinoline-2,8-dicarboxylate
• CAS: 114184-12-2
• 化学式: C₂₂H₁₈F₅NO₆
• 分子量: 487.38
• InChiKey: SQDCTRGLLKYQEB-UHFFFAOYSA-N

物化性质

• 熔点：
  136-139 °C
• 沸点：
  548.7±50.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  91.8
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  ethyl methyl 4-oxo-6-(pentafluoroethyl)-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.25h， 以75%的产率得到disodium 4-oxo-6-(pentafluoroethyl)-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate
  参考文献：
  名称：

  Predictive structure-activity relationships in a series of pyranoquinoline derivatives. A new primate model for the identification of antiallergic activity

  摘要：

  A new primate model has been developed for the evaluation of antiallergic agents. Compounds are tested for their ability to inhibit anti-IgE induced histamine release from the bronchoalveolar mast cells lavaged from the lungs of Macaca arctoides infected with the parasite Ascaris suum. A number of 6-substituted pyranoquinoline derivatives have been evaluated and the activities were subjected to Hansch analysis. A highly significant correlation with lipophilicity (pi) and Hammett sigma p values was obtained. The relationship was used to predict further compounds for synthesis giving rise to new, potent analogues. Some apparently anomalous results could be explained by differences in the ionization of, or tautomerism in, the quinoline ring.

  DOI：

  10.1021/jm00402a033
• 作为产物：
  描述：

  2-ethyl 8-methyl 6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate 在 铜 、 三溴氧磷 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 ethyl methyl 4-oxo-6-(pentafluoroethyl)-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate
  参考文献：
  名称：

  Predictive structure-activity relationships in a series of pyranoquinoline derivatives. A new primate model for the identification of antiallergic activity

  摘要：

  A new primate model has been developed for the evaluation of antiallergic agents. Compounds are tested for their ability to inhibit anti-IgE induced histamine release from the bronchoalveolar mast cells lavaged from the lungs of Macaca arctoides infected with the parasite Ascaris suum. A number of 6-substituted pyranoquinoline derivatives have been evaluated and the activities were subjected to Hansch analysis. A highly significant correlation with lipophilicity (pi) and Hammett sigma p values was obtained. The relationship was used to predict further compounds for synthesis giving rise to new, potent analogues. Some apparently anomalous results could be explained by differences in the ionization of, or tautomerism in, the quinoline ring.

  DOI：

  10.1021/jm00402a033

文献信息

• GOULD, KEN J.;MANNERS, CAROL N.;PAYLING, DAVID W.;SUSCHITZKY, JOHN L.;WEL+, J. MED. CHEM., 31,(1988) N 7, 1445-1453
  作者：GOULD, KEN J.、MANNERS, CAROL N.、PAYLING, DAVID W.、SUSCHITZKY, JOHN L.、WEL+

  DOI：——

  日期：——
• Predictive structure-activity relationships in a series of pyranoquinoline derivatives. A new primate model for the identification of antiallergic activity
  作者：Ken J. Gould、Carol N. Manners、David W. Payling、John L. Suschitzky、Edward Wells

  DOI：10.1021/jm00402a033

  日期：1988.7

  A new primate model has been developed for the evaluation of antiallergic agents. Compounds are tested for their ability to inhibit anti-IgE induced histamine release from the bronchoalveolar mast cells lavaged from the lungs of Macaca arctoides infected with the parasite Ascaris suum. A number of 6-substituted pyranoquinoline derivatives have been evaluated and the activities were subjected to Hansch analysis. A highly significant correlation with lipophilicity (pi) and Hammett sigma p values was obtained. The relationship was used to predict further compounds for synthesis giving rise to new, potent analogues. Some apparently anomalous results could be explained by differences in the ionization of, or tautomerism in, the quinoline ring.