ethyl methyl 6-bromo-4-oxo-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate | 99370-25-9

• 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 6-bromo-4-oxo-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate
• 英文别名: ethyl methyl 6-bromo-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate；2-O-ethyl 8-O-methyl 6-bromo-4-oxo-10-propylpyrano[3,2-g]quinoline-2,8-dicarboxylate
• CAS: 99370-25-9
• 化学式: C₂₀H₁₈BrNO₆
• 分子量: 448.27
• InChiKey: XMJXITVFMGJPCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl methyl 6-bromo-4-oxo-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate 在 sodium hydroxide 、 铜 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 4.25h， 生成 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 三溴氧磷 作用下， 生成 ethyl methyl 6-bromo-4-oxo-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate
  参考文献：
  名称：

  新的抗过敏性吡喃并[3,2-g]喹啉-2,8-二羧酸，可能会局部治疗哮喘。

  摘要：

  已经合成了许多潜在用于哮喘局部治疗的抗过敏性吡喹啉二羧酸衍生物。所有化合物均已针对大鼠被动皮肤过敏反应和狗低血压筛查进行了评估。这是后一种筛选方法用于识别抗过敏剂的第一个详细说明。两种化合物，9-乙基-6钠，9-二氢-4,6-二氧代-10-丙基-4H-吡喃[3,2-g]喹啉-2,8-二羧酸酯（86）和6-（甲氨基二钠） ）-4-氧代-10-丙基-4H-吡喃并[3,2-g]-喹啉-2，8-二羧酸酯（72），并进一步评估了它们诱导78000分子量相关蛋白磷酸化的能力与大鼠腹膜肥大细胞。还已经评估了它们抑制组胺从这些细胞和粘膜肥大细胞制剂中释放的能力。这些化合物，奈多克罗米钠（TILADE 86）和米诺克罗米尔（72的游离酸），目前正在接受治疗评估。讨论了筛选程序的原理以及这些二元酸的第二羧酸功能与受体结合的相关性。

  DOI：

  10.1021/jm00150a014

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：——
• New antiallergic pyrano[3,2-g]quinoline-2,8-dicarboxylic acids with potential for the topical treatment of asthma
  作者：Hugh Cairns、David Cox、Ken J. Gould、Anthony H. Ingall、John L. Suschitzky

  DOI：10.1021/jm00150a014

  日期：1985.12

  Their ability to inhibit histamine release from these cells and from a mucosal mast cell preparation has also been evaluated. These compounds, nedocromil sodium (TILADE 86) and minocromil (the free acid of 72), are at present undergoing therapeutic evaluation. The rationale for the screening procedure and the relevance of the second carboxylic acid function of these dibasic acids to receptor binding are

  已经合成了许多潜在用于哮喘局部治疗的抗过敏性吡喹啉二羧酸衍生物。所有化合物均已针对大鼠被动皮肤过敏反应和狗低血压筛查进行了评估。这是后一种筛选方法用于识别抗过敏剂的第一个详细说明。两种化合物，9-乙基-6钠，9-二氢-4,6-二氧代-10-丙基-4H-吡喃[3,2-g]喹啉-2,8-二羧酸酯（86）和6-（甲氨基二钠） ）-4-氧代-10-丙基-4H-吡喃并[3,2-g]-喹啉-2，8-二羧酸酯（72），并进一步评估了它们诱导78000分子量相关蛋白磷酸化的能力与大鼠腹膜肥大细胞。还已经评估了它们抑制组胺从这些细胞和粘膜肥大细胞制剂中释放的能力。这些化合物，奈多克罗米钠（TILADE 86）和米诺克罗米尔（72的游离酸），目前正在接受治疗评估。讨论了筛选程序的原理以及这些二元酸的第二羧酸功能与受体结合的相关性。
• 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.