diethyl 6-(dimethylamino)-4-oxo-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate | 75453-52-0

• 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: diethyl 6-(dimethylamino)-4-oxo-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate
• 英文别名: Diethyl 6-dimethylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate；diethyl 6-(dimethylamino)-4-oxo-10-propylpyrano[3,2-g]quinoline-2,8-dicarboxylate
• CAS: 75453-52-0
• 化学式: C₂₃H₂₆N₂O₆
• 分子量: 426.469
• InChiKey: MOCFMNUYCSTIKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  95
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 6-(dimethylamino)-4-oxo-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78%的产率得到disodium 6-(dimethylamino)-4-oxo-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：

  methyl 6-acetyl-4-chloro-7-hydroxy-8-propylquinoline-2-carboxylate 在 盐酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 57.0h， 生成 diethyl 6-(dimethylamino)-4-oxo-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

• Pyranoquinolinones and analogs thereof
  申请人：Fisons Limited

  公开号：US04419352A1

  公开（公告）日：1983-12-06

  There are described compounds of formula I, ##STR1## in which an adjacent pair of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a chain --CZC(G.sub.1).dbd.(G.sub.2)--Z--, R.sub.4, R.sub.9 and the remainder of R.sub.5, R.sub.6, R.sub.7 and R.sub.8, which may be the same or different, each represent hydrogen, alkyl, halogen, alkenyl, --NO.sub.2, --NR.sub.1 R.sub.2, --OR.sub.3, --S(O).sub.n R.sub.3 ; or alkyl substituted by hydroxy, amino, alkoxy or carbonyl oxygen, n is 0, 1 or 2, R.sub.1 and R.sub.2, which may be the same or different, each represent hydrogen, alkyl, --CONHR.sub.3, phenyl or phenyl substituted by alkyl or halogen, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a 5 or 6 membered heterocyclic ring, R.sub.3 represents hydrogen, alkyl, alkenyl or phenyl, one of G.sub.1 and G.sub.2 is hydrogen and the other is a group E, each E, which may be the same or different, is --COOH, a 5-tetrazolyl group, or a carboxamidotetrazole group, each Z, which may be the same or different, is oxygen or sulphur, and one or two of the atoms, a, b, c and d are nitrogen atoms and the remainder are carbon atoms, R.sup.9 having no significance when two of a, b, c and d are nitrogen, (with certain exclusions) and pharmaceutically acceptable derivatives thereof. There are also described methods for making the compounds and pharmaceutical, e.g. anti-allergic, compositions and mixtures containing them.

  本文描述了I式化合物，其中相邻的R.sub.5、R.sub.6、R.sub.7和R.sub.8形成链--CZC(G.sub.1).dbd.(G.sub.2)--Z--，R.sub.4、R.sub.9和R.sub.5、R.sub.6、R.sub.7和R.sub.8的其余部分，可以相同或不同，分别表示氢、烷基、卤素、烯基、--NO.sub.2、--NR.sub.1R.sub.2、--OR.sub.3、--S(O).sub.nR.sub.3；或者被羟基、氨基、烷氧基或羰基氧代替的烷基，其中n为0、1或2，R.sub.1和R.sub.2可以相同或不同，分别表示氢、烷基、--CONHR.sub.3、苯基或被烷基或卤素取代的苯基，或者R.sub.1和R.sub.2与它们附着的氮原子一起形成5或6元杂环环，R.sub.3表示氢、烷基、烯基或苯基，G.sub.1和G.sub.2中的一个是氢，另一个是E基团，每个E基团可以相同或不同，分别为--COOH、5-四唑基团或羧酰基四唑基团，每个Z可以相同或不同，分别为氧或硫，其中a、b、c和d中有一个或两个是氮原子，其余是碳原子，当a、b、c和d中有两个是氮原子时，R.sup.9没有意义（有一定的排除），以及其药学上可接受的衍生物。还描述了制备这些化合物的方法以及含有它们的药物，例如抗过敏的组合物和制剂。
• 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：——
• US4419352A
  申请人：——

  公开号：US4419352A

  公开（公告）日：1983-12-06
• 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.