methyl 6-acetyl-4-chloro-7-hydroxy-8-propylquinoline-2-carboxylate | 75452-57-2

• 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: methyl 6-acetyl-4-chloro-7-hydroxy-8-propylquinoline-2-carboxylate
• CAS: 75452-57-2
• 化学式: C₁₆H₁₆ClNO₄
• 分子量: 321.76
• InChiKey: QZYQVGZTJCZYSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-acetyl-4-chloro-7-hydroxy-8-propylquinoline-2-carboxylate 在 盐酸 、 sodium hydroxide 、 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 58.25h， 生成 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-1,4-dihydro-7-hydroxy-4-oxo-8-propylquinoline-2-carboxylate 在 三氯氧磷 作用下， 以 苯 为溶剂， 反应 25.0h， 以88%的产率得到methyl 6-acetyl-4-chloro-7-hydroxy-8-propylquinoline-2-carboxylate
  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

• 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.

  描述了具有I式化合物，其中相邻的R.sub.5、R.sub.6、R.sub.7和R.sub.8形成一个链--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，它们可能相同也可能不同，分别代表氢、烷基、卤素、烯基、-NO.sub.2、-NR.sub.1 R.sub.2、-OR.sub.3、-S(O).sub.n R.sub.3；或被羟基、氨基、烷氧基或酰氧基取代的烷基，n为0、1或2，R.sub.1和R.sub.2，它们可能相同也可能不同，分别代表氢、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与它们连接的氮原子一起形成5或6元杂环环，R.sub.3代表氢、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，可能相同也可能不同，是-羧基、5-四唑基团或羧酰氨基四唑基团，每个Z，可能相同也可能不同，是氧或硫，a、b、c和d中的一个或两个是氮原子，其余是碳原子，当a、b、c和d中两个是氮时，R.sup.9没有意义（具体排除了某些情况），以及其药用可接受的衍生物。还描述了制备这些化合物的方法以及含有它们的制药、例如抗过敏、组合物和混合物。
• Anti-allergic mono salt of
  申请人：Fisons Limited

  公开号：US04356181A1

  公开（公告）日：1982-10-26

  There is described the mono salt of 6-methylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]-quinoline-2,8-dicarboxylic acid with a strongly basic cation. There is also described an aqueous solution of 6-methylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid the solution being at a pH of from 4 to 8. The salts and solutions are useful as pharmaceuticals, e.g. in the treatment of allergies.

  本文描述了6-甲氨基-4-氧代-10-丙基-4H-吡喃并[3,2-g]-喹啉-2,8-二羧酸的单盐，其与强碱性阳离子结合。还描述了一种6-甲氨基-4-氧代-10-丙基-4H-吡喃并[3,2-g]喹啉-2,8-二羧酸的水溶液，该溶液的pH值在4至8之间。这些盐和溶液可用于制药，例如用于过敏症的治疗。
• Salts and aqueous solutions of 6-methylamino-4-oxo-10-propyl-4H-pyrano(3,2-g)-quinoline-2,8-di-carboxylic acid and pharmaceutical compositions containing such salts and solutions
  申请人：FISONS plc

  公开号：EP0037187A1

  公开（公告）日：1981-10-07

  There is described the mono salt of 6-methylamino-4-oxo-10-propyl-4H-pyrano(3,2-g)quinoline- 2,8-dicarboxylic acid with a strongly basic cation. There is also described an aqueous solution of 6-methyl- amino-4-oxo-10-propyl-4H- pyrano(3,2--g)quinoline-2,8-dicarboxylic acid the solution being at a pH of from 4 to 8. The salts and solutions are useful as pharmaceuticals, e.g. in the treatment of allergies.

  6- 甲基氨基-4-氧代-10-丙基-4H-吡喃(3,2-g)喹啉-2,8-二羧酸的单盐具有强碱性阳离子。 还描述了一种 6-甲基-氨基-4-氧代-10-丙基-4H-吡喃并(3,2-g)喹啉-2,8-二甲酸的水溶液，该溶液的 pH 值为 4 至 8。 这些盐和溶液可用作药物，例如治疗过敏症。
• CAIRNS, H.;COX, D.;GOULD, K. J.;INGALL, A. H.;SUSCHITZKY, J. L., J. MED. CHEM., 1985, 28, N 12, 1832-1842
  作者：CAIRNS, H.、COX, D.、GOULD, K. J.、INGALL, A. H.、SUSCHITZKY, J. L.

  DOI：——

  日期：——
• 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：——