1-[8-甲氧基-4-(2-甲基苯胺基)喹啉-3-基]乙酮 | 115607-60-8

• 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
• 中文名称: 1-[8-甲氧基-4-(2-甲基苯胺基)喹啉-3-基]乙酮
• 英文名称: 3-acetyl-4-(2-methylphenylamino)-8-methoxyquinoline
• 英文别名: 1-[8-methoxy-4-(2-methylanilino)quinolin-3-yl]ethanone
• CAS: 115607-60-8
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: ZLGHFBJWCWKOHS-UHFFFAOYSA-N

物化性质

• 沸点：
  450.0±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[8-甲氧基-4-(2-甲基苯胺基)喹啉-3-基]乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 以75%的产率得到1-(8-Methoxy-4-o-tolylamino-quinolin-3-yl)-ethanol
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4-(phenylamino)quinolines

  摘要：

  Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4-arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show th bearing such a substituent, only a particular combination of properties provides high activity, both in as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a pi-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK&F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00096a018
• 作为产物：
  描述：

  2-acetyl-3-o-anisidino-acrylic acid ethyl ester 在 三氯氧磷 作用下， 以 1,4-二氧六环 、 二苯醚 为溶剂， 反应 3.75h， 生成 1-[8-甲氧基-4-(2-甲基苯胺基)喹啉-3-基]乙酮
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4-(phenylamino)quinolines

  摘要：

  Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4-arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show th bearing such a substituent, only a particular combination of properties provides high activity, both in as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a pi-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK&F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00096a018

文献信息

• 4-amino-3-carbonyl substituted quinolines
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04806549A1

  公开（公告）日：1989-02-21

  This invention relates to novel substituted 4-aminoquinoline derivatives which are inhibitors of gastric acid secretion in mammals. A compound of the invention is 3-butyryl-4-(2-methylphenylamino)-8-methoxyquinoline.

  这项发明涉及新型的取代4-氨基喹啉衍生物，它们是哺乳动物胃酸分泌抑制剂。该发明的化合物是3-丁酰基-4-(2-甲基苯胺基)-8-甲氧基喹啉。
• 4-Amino-3-carbonyl substituted quinolines as inhibitors of gastric acid
  申请人：SmithKline & French Laboratories Limited

  公开号：US04806550A1

  公开（公告）日：1989-02-21

  This invention relates to novel substituted 4-aminoquinoline derivatives which are inhibitors of gastric acid secretion in mammals. A compound of the invention is 3-butyryl-4-(2-methylphenylamino)-8-methoxyquinoline.

  本发明涉及一种新型的取代的4-氨基喹啉衍生物，该衍生物是哺乳动物胃酸分泌抑制剂。本发明的一种化合物是3-丁酰基-4-(2-甲基苯胺基)-8-甲氧基喹啉。
• Derivatives of 4-aminoquinoline and their use as medicaments
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0259174B1

  公开（公告）日：1992-03-18
• US4806549A
  申请人：——

  公开号：US4806549A

  公开（公告）日：1989-02-21
• US4806550A
  申请人：——

  公开号：US4806550A

  公开（公告）日：1989-02-21