3-((3-ethoxycarbonyl)propionyl)-4-hydroxy-8-methoxyquinoline | 150620-61-4

• 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: 3-((3-ethoxycarbonyl)propionyl)-4-hydroxy-8-methoxyquinoline
• 英文别名: 3-(3-ethoxycarbonylpropionyl)-4-hydroxy-8-methoxyquinoline；ethyl 4-(8-methoxy-4-oxo-1H-quinolin-3-yl)-4-oxobutanoate
• CAS: 150620-61-4
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: DLEFMUJJONREFK-UHFFFAOYSA-N

物化性质

• 沸点：
  478.6±45.0 °C(predicted)
• 密度：
  1.262±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-((3-ethoxycarbonyl)propionyl)-4-hydroxy-8-methoxyquinoline 在 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 乙基4-[8-甲氧基-4-[(2-甲基苯基)氨基]喹啉-3-基]-4-氧代丁酸酯
  参考文献：
  名称：

  Inhibition of bone resorption by H+/K+-ATPase inhibitors

  摘要：

  We have found that 3-(3-(ethoxycarbonyl)propionyl)-8-methoxy-4-((2-methylphenyl)amino)quinoline (1, CP-113,411), a reversible inhibitor of gastric H+/K+-ATPase (IC50 10-20 mM), is also a potent inhibitor of bone resorption by osteoclasts in a bone slice assay at concentrations as low as 10(-7) M, with an IC50 of 2 mM. By contrast, the structurally related H+/K+-ATPase inhibitor 2 (3-(ethoxycarbonyl)-8-methoxy-4-((2-methylphenyl)amino)quinoline) disclosed by Robins is slightly more potent as an inhibitor of the gastric enzyme (IC50 3-10 muM in our hands) but less efficacious than 1 as an inhibitor of osteoclasts in the bone slice assay at the lower concentrations (no effect at less-than-or-equal-to 10(-6) M, IC50 4 mM). These findings suggest that osteoclasts contain an H+/K+-ATPase-like enzyme which differs from the gastric one.

  DOI：

  10.1021/jm00071a014
• 作为产物：
  描述：

  3-氧代己二酸二乙酯 在 二苯醚 作用下， 反应 7.0h， 生成 3-((3-ethoxycarbonyl)propionyl)-4-hydroxy-8-methoxyquinoline
  参考文献：
  名称：

  Inhibition of bone resorption by H+/K+-ATPase inhibitors

  摘要：

  We have found that 3-(3-(ethoxycarbonyl)propionyl)-8-methoxy-4-((2-methylphenyl)amino)quinoline (1, CP-113,411), a reversible inhibitor of gastric H+/K+-ATPase (IC50 10-20 mM), is also a potent inhibitor of bone resorption by osteoclasts in a bone slice assay at concentrations as low as 10(-7) M, with an IC50 of 2 mM. By contrast, the structurally related H+/K+-ATPase inhibitor 2 (3-(ethoxycarbonyl)-8-methoxy-4-((2-methylphenyl)amino)quinoline) disclosed by Robins is slightly more potent as an inhibitor of the gastric enzyme (IC50 3-10 muM in our hands) but less efficacious than 1 as an inhibitor of osteoclasts in the bone slice assay at the lower concentrations (no effect at less-than-or-equal-to 10(-6) M, IC50 4 mM). These findings suggest that osteoclasts contain an H+/K+-ATPase-like enzyme which differs from the gastric one.

  DOI：

  10.1021/jm00071a014

文献信息

• Aminoquinoline derivatives
  申请人：Pfizer Inc.

  公开号：US05362743A1

  公开（公告）日：1994-11-08

  Certain novel 3-acyl-4-amino-8-alkoxyquinoline compounds have been prepared, including their pharmaceutically-acceptable salts. These compounds are useful for inhibiting gastric acid secretion in mammals and therefore, are of value in therapy as anti-ulcer agents. They are also useful for treating osteoporosis in a mammalian subject afflicted with said condition. Methods for preparing these compounds from known starting materials are provided.

  已经合成了某些新型的3-酰基-4-氨基-8-烷氧基喹啉化合物，包括它们的药学上可接受的盐。这些化合物对于抑制哺乳动物的胃酸分泌很有用，因此在治疗抗溃疡剂方面具有价值。它们还可用于治疗患有骨质疏松症的哺乳动物。提供了从已知起始材料制备这些化合物的方法。
• US5362743A
  申请人：——

  公开号：US5362743A

  公开（公告）日：1994-11-08
• Inhibition of bone resorption by H+/K+-ATPase inhibitors
  作者：Reinhard Sarges、Andrea Gallagher、Timothy J. Chambers、Li-An Yeh

  DOI：10.1021/jm00071a014

  日期：1993.9

  We have found that 3-(3-(ethoxycarbonyl)propionyl)-8-methoxy-4-((2-methylphenyl)amino)quinoline (1, CP-113,411), a reversible inhibitor of gastric H+/K+-ATPase (IC50 10-20 mM), is also a potent inhibitor of bone resorption by osteoclasts in a bone slice assay at concentrations as low as 10(-7) M, with an IC50 of 2 mM. By contrast, the structurally related H+/K+-ATPase inhibitor 2 (3-(ethoxycarbonyl)-8-methoxy-4-((2-methylphenyl)amino)quinoline) disclosed by Robins is slightly more potent as an inhibitor of the gastric enzyme (IC50 3-10 muM in our hands) but less efficacious than 1 as an inhibitor of osteoclasts in the bone slice assay at the lower concentrations (no effect at less-than-or-equal-to 10(-6) M, IC50 4 mM). These findings suggest that osteoclasts contain an H+/K+-ATPase-like enzyme which differs from the gastric one.