3-butyryl-4-chloro-8-methylquinoline | 115607-96-0

• 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-butyryl-4-chloro-8-methylquinoline
• 英文别名: 1-(4-chloro-8-methylquinolin-3-yl)butan-1-one
• CAS: 115607-96-0
• 化学式: C₁₄H₁₄ClNO
• 分子量: 247.724
• InChiKey: RXOVQHSFOZRJPT-UHFFFAOYSA-N

物化性质

• 沸点：
  344.7±37.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-butyryl-4-chloro-8-methylquinoline 、 2-甲基-4-甲氧基苯胺 在 碳酸氢钠 、 甲醇 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以gave 3-butyryl-4-(4-methoxy-2-methylphenylamino)-8-methylquinoline (5.30 g), m.p. 114°-115°的产率得到3-butyryl-4-(4-methoxy-2-methylphenylamino)-8-methylquinoline
  参考文献：
  名称：

  4-amino-3-carbonyl substituted quinolines

  摘要：

  本发明涉及一种新型的取代的4-氨基喹啉衍生物，其为哺乳动物胃酸分泌抑制剂。该发明的化合物为3-丁酰基-4-(2-甲基苯胺基)-8-甲氧基喹啉。

  公开号：

  US04806549A1
• 作为产物：
  描述：

  2-(乙氧基亚甲基)-3-氧代-己酸乙酯 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 2.75h， 生成 3-butyryl-4-chloro-8-methylquinoline
  参考文献：
  名称：

  Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 4. Identification of an Inhibitor with an Intermediate Duration of Action

  摘要：

  3-Acyl-4-(arylamino)quinolines were previously identified as gastric (H+/K+)-ATPase inhibitors, and clinical efficacy has been demonstrated for compound 3 (SK&F 96067). In the present study the further structure-activity relationship of this series is developed. Only a limited range of substituents are tolerated on the N-aryl ring or the 6- and 7-positions of the quinoline, and although hydroxylated derivatives were identified possessing markedly greater affinity for the enzyme, none of these proved to have adequate potency after oral dosing. In contrast, the 8-position of the quinoline ring proved suitable for a wide variety of substituents, allowing modification of physicochemical properties while retaining primary activity. This led to the identification of compound 4 (SK&F 97574), which combines good oral potency with a somewhat longer duration of action than 3 (though much shorter than covalent inhibitors such as omeprazole). This compound was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00014a026

文献信息

• 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
• [EN] 4-AMINOQUINOLINE DERIVATIVES AND THEIR USE AS MEDICAMENTS
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：WO1988001621A1

  公开（公告）日：1988-03-10

  (EN) Compounds of structure (I), in which R1 is hydrogen, C1-6alkyl, C1-6alkoxyl-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, phenyl, phenyl-C1-6alkyl, the phenyl groups being optionally substituted; R2 is C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, phenyl, phenylC1-6alkyl or phenyl substituted by 1-3 radicals selected from C1-6alkyl, C1-6alkoxy, amino C1-6alkylthio, halogen, cyano, hydroxy, carbamoyl, carboxy, C1-6alkanoyl, trifluoromethyl and nitro; R3 is C1-6alkyl, phenyl, C1-6alkoxy, C1-6alkylthio, C1-6alkanoyl, amino, C1-6alkylamino, di-C1-6alkylamino, halogen, trifluoromethyl or cyano; and n is 0, 1 or 2, or pharmaceutically acceptable salts thereof, processes for their preparation, pharmaceutical compositions containing them and their use in therapy for the inhibition of gastric acid secretion.(FR) Composés de structure (I), dans laquelle R1 est hydrogène, alkyle C1-6, alkoxy C1-6 alkyle C1-6, cycloalkyle C3-6, cycloalkyle C3-6, alkyle C1-6, phényle, phénylalkyle C1-6, les groupes phényle étant éventuellement substitués; R2 est alkyle C1-6, cycloalkyle C3-6, cycloalkyle C3-6 alkyle C1-6, phényle, phénylalkyle C1-6 ou phényle substitué par 1 à 3 radicaux sélectionnés parmi alkyle C1-6, alkoxy C1-6, amino-alkylthio C1-6, halogène, cyano, hydroxy, carbamoyle, carboxy, alkanoyle C1-6, trifluorométhyle et nitro; R3 est alkyle C1-6, trifluorométhyle et nitro; R3 est alkyle C1-6, phényle, alkoxy C1-6, alkylthio C1-6, alkanoyle C1-6, amino alkylamino C1-6, dialkylamino C1-6, halogène, trifluorométhyle ou cyano; n vaut 0, 1 ou 2. Sont également décrits des sels pharmaceutiquement acceptables desdits composés, leurs procédés de préparation, compositions pharmaceutiques les contenant et leur utilisation thérapeutique pour inhiber la sécrétion d'acides gastriques.