3-Isobutyryl-8-methoxy-4(1H)-quinolone | 115607-92-6

• 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-Isobutyryl-8-methoxy-4(1H)-quinolone
• 英文别名: 8-methoxy-3-(2-methylpropanoyl)-1H-quinolin-4-one
• CAS: 115607-92-6
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: WBKBZFSYSORVJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Isobutyryl-8-methoxy-4(1H)-quinolone 在 三氯氧磷 作用下， 以 Petroleum ether 为溶剂， 生成 3-isobutyryl-4-chloro-8-methoxy-quinoline
  参考文献：
  名称：

  Substituted 4-aminoquinoline derivatives as gastric acid secretion

  摘要：

  公式为：##STR1##其中R.sup.1是氢，C.sub.1-6烷基，C.sub.1-6烷氧基，C.sub.1-6烷氧基C.sub.1-6烷基，C.sub.3-6环烷基，C.sub.3-6环烷基C.sub.1-6烷基，苯基C.sub.1-6烷基，苯基可以选择性地被取代；R.sup.2是氢，C.sub.1-6烷基，C.sub.1-6烷氧基，氨基，C.sub.1-6烷基硫基，卤素，氰基，羟基，氨甲酰基，羧基，C.sub.1-6烷酰基或三氟甲基；m为1至3；p为0至4；R.sup.3是COR.sup.4；R.sup.4是羟基，C.sub.1-6烷氧基或NR.sup.5 R.sup.6；R.sup.5和R.sup.6分别是氢或C.sub.1-6烷基，或者与它们连接的氮原子一起形成杂环环；R.sup.7是氢，C.sub.1-6烷氧基或C.sub.1-6烷基；或其盐。

  公开号：

  US05089504A1
• 作为产物：
  描述：

  ethyl 3-<(2-methoxyphenyl)amino>acrylate 在 sodium hydride 作用下， 以 二苯醚 为溶剂， 反应 17.5h， 生成 3-Isobutyryl-8-methoxy-4(1H)-quinolone
  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。
• Substituted 4-aminoquinoline derivatives as gastric acid secretion
  申请人：SmithKline Beckman Intercredit B.V.

  公开号：US05089504A1

  公开（公告）日：1992-02-18

  Substituted 4-aminoquinazoline derivatives of the formula: ##STR1## in which R.sup.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkoxyC.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkylC.sub.1-6 alkyl, phenylC.sub.1-6 alkyl, the phenyl group being optionally substituted; R.sup.2 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, amino, C.sub.1-6 alkylthio, halogen, cyano, hydroxy, carbamoyl, carboxy, C.sub.1-6 alkanoyl or trifluoromethyl; m is 1 to 3; p is 0 to 4; R.sup.3 is COR.sup.4 ; R.sup.4 is hydroxy, C.sub.1-6 alkoxy, or NR.sup.5 R.sup.6 ; R.sup.5 and R.sup.6 are each hydrogen or C.sub.1-6 alkyl or together with the nitrogen atom to which they are attached form a heterocyclic ring; and R.sup.7 is hydrogen, C.sub.1-6 alkoxy or C.sub.1-6 alkyl; or a salt thereof.

  公式为：##STR1##其中R.sup.1是氢，C.sub.1-6烷基，C.sub.1-6烷氧基，C.sub.1-6烷氧基C.sub.1-6烷基，C.sub.3-6环烷基，C.sub.3-6环烷基C.sub.1-6烷基，苯基C.sub.1-6烷基，苯基可以选择性地被取代；R.sup.2是氢，C.sub.1-6烷基，C.sub.1-6烷氧基，氨基，C.sub.1-6烷基硫基，卤素，氰基，羟基，氨甲酰基，羧基，C.sub.1-6烷酰基或三氟甲基；m为1至3；p为0至4；R.sup.3是COR.sup.4；R.sup.4是羟基，C.sub.1-6烷氧基或NR.sup.5 R.sup.6；R.sup.5和R.sup.6分别是氢或C.sub.1-6烷基，或者与它们连接的氮原子一起形成杂环环；R.sup.7是氢，C.sub.1-6烷氧基或C.sub.1-6烷基；或其盐。
• Compounds substituted quinoline derivatives
  申请人：SmithKline Beecham Intercredit B.V.

  公开号：US05432182A1

  公开（公告）日：1995-07-11

  Substituted 4-aminoquinazoline derivatives which are inhibitors of gastric acid secretion. A compound of the invention are the salts of strong acids of 3-butyryl-4-(2-methylphenylamino)-8-(hydroxymethyl)quinoline.

  替代4-氨基喹唑啉衍生物是胃酸分泌抑制剂。该发明的化合物是3-丁酰基-4-(2-甲基苯胺基)-8-(羟甲基)喹啉的强酸盐。
• 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。
• 4-Amino-3-acyl quinoline derivatives and their use as inhibitors of gastric acid secretion
  申请人：SmithKline Beecham Intercredit B.V.

  公开号：EP0330485A1

  公开（公告）日：1989-08-30

  Compounds of structure (I) in which R1 is hydrogen, C1-6alkyl, C1-6alkoxy, C1-6al- koxyC1-6-alkyl, C3-6cycloalkyl, C3-6cycloalkylC1-6alkyl, phenyl, phenylC1-6alkyl, the phenyl groups being optionally substituted; R2 is hydrogen, C1-6alkyl, C1-6alkoxy, amino, C1-6-alkylthio, halogen, cyano, hydroxy, carbamoyl, carboxy; Ci-salka- noyl or trifluoromethyl; m is 1, 2 or 3; p is 0 to 4; R3 is hydroxyC1-6alkyl, polyhydroxyC1-6alkyl, C1-6alkoxy1-6alkyl, hy- droxyC1-6alkoxy, polyhydroxyC1-6alkoxy, C1-6alkoxyC1-6alkoxy or hydroxyC1-6alkoxyC1-6alkoxy; and R4 is hydrogen, hydroxy, Ci-salkyl, or C1-6alkoxy, processes for their preparation, intermediates useful in their preparation, pharmaceutical compositions containing them and their use in therapy as inhibitors of gastric acid secretion.

  结构(I)的化合物 其中 R1 是氢、C1-6烷基、C1-6烷氧基、C1-6al- koxyC1-6-烷基、C3-6 环烷基、C3-6 环烷基 C1-6烷基、苯基、苯基 C1-6烷基，苯基基团被任选取代；R2 是氢、C1-6烷基、C1-6烷氧基、氨基、C1-6-烷硫基、卤素、氰基、羟基、氨基甲酰基、羧基、Ci-salka- noyl 或三氟甲基；m 是 1、2 或 3；p 是 0 至 4；R3 是羟基 C1-6烷基、多羟基 C1-6烷基、C1-6烷氧基 C1-6烷基、羟基 C1-6烷氧基、多羟基 C1-6烷氧基、C1-6烷氧基 C1-6烷氧基或羟基 C1-6烷氧基 C1-6烷氧基；以及 R4 是氢、羟基、Ci-烷基或 C1-6烷氧基、它们的制备工艺、制备它们时有用的中间体、含有它们的药物组合物以及它们作为胃酸分泌抑制剂在治疗中的用途。