1-methyl-2-oxo-6-propionyl-1,2,3,4-tetrahydroquinoline | 73470-82-3

• 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: 1-methyl-2-oxo-6-propionyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-methyl-6-propanoyl-3,4-dihydroquinolin-2-one
• CAS: 73470-82-3
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: HSRGNAOYZDXKOW-UHFFFAOYSA-N

物化性质

• 沸点：
  474.7±45.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-2-oxo-6-propionyl-1,2,3,4-tetrahydroquinoline 、 2,3-二氯-5,6-二氰基-1,4-苯醌 在 silica gel 、 苯 、 乙酸乙酯 作用下， 以 苯 为溶剂， 反应 24.0h， 以to give an oil of 1-methyl-2-oxo-6-propionyl-1,2-dihydroquinoline (7.72 g)的产率得到1-Methyl-6-propionyl-2(1H)-chinolon
  参考文献：
  名称：

  Triazine derivatives, and pharmaceutical compositions comprising the same

  摘要：

  新的三嗪衍生物的化学式为：##STR1## 其中R.sup.1是1,2,3,4-四氢喹啉基，2-氧代-1,2,3,4-四氢喹啉基，2-氧代-1,2-二氢喹啉基，吲哚基，2-氧代吲哚基，苯并噻唑基，2-氧代苯并噻唑啉基，3,4-二氢-1H-2,1-苯并噻唑基，其中S原子可选择氧化，或3-氧代-2,3-二氢-4H-1,4-苯并噁唑基，每个基团都可以有一个或多个取代基，所述取代基包括低碳基、羟基(低)碳基、低烷氨基、低烷酰基、环状低烷酰基、低烷氧基(低)烷基、低烷氨基(低)烷酰基、苄基、苄氧基(低)烷基、低烷氧羰基(低)烷基和4-(2-羟乙基)哌嗪-1-基甲酰甲基；R.sup.2是氢、低烯基、苄基、羧基(低)烷基或低烷氧基羰基(低)烷基；R.sup.3和R.sup.4，可以相同也可以不同，都是氢或低烷基，或者一起表示一个键；但是当R.sup.1是未取代或取代了一个低烷基的2-氧代-1,2,3,4-四氢喹啉基时，则R.sup.4是氢或R.sup.2是低烯基、苄基、羧基(低)烷基或低烷氧基羰基(低)烷基；以及其药学上可接受的盐，用于治疗人类和动物的高血压、血栓和溃疡。

  公开号：

  US04581356A1
• 作为产物：
  描述：

  1-甲基-3,4-二氢-1H-喹啉-2-酮 、 丙酰氯 在 三氯化铝 、 N,N-二甲基甲酰胺 作用下， 反应 1.0h， 生成 1-methyl-2-oxo-6-propionyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Dihydropyridazinone cardiotonics. The discovery and inotropic activity of 1,3-dihydro-3,3-dimethyl-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-indol-2-one

  摘要：

  We discovered that 6 (N-[4-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)phenyl]acetamide) is a potent positive inotrope in dogs, and we have prepared several lactam analogues of this agent. These included 16 (1,3-dihydro-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-indol-2-one), 32 (the analogous quinolin-2-one), and 37 (the analogous benzazepin-2-one). The inotropic ED50's of these compounds were 24, 3.3, and 5.2 micrograms/kg, respectively, after iv administration to pentobarbital-anesthetized dogs. Compound 20 (LY195115, 1,3-dihydro-3,3-dimethyl-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-i ndol-2- one), the geminal dimethyl analogue of 16, was 3.5-fold more potent than 16 when administered iv (ED50 = 6.8 micrograms/kg). However, the most profound effect of the geminal alkyl substitution was on oral activity. The approximate ED50's of 20 and 16 after oral administration to conscious dogs were 25 and 400 micrograms/kg, respectively. The increase in contractility produced by 25 micrograms/kg of 20 was maximally sustained in excess of 8 h. Thus, 20 is one of the most potent and long-acting oral inotropes described to date.

  DOI：

  10.1021/jm00160a006

文献信息

• Triazine derivatives, processes for preparation thereof and pharmaceutical compositions comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0122494A2

  公开（公告）日：1984-10-24

  New triazine derivatives represented by the formula: wherein R' is a 1, 2, 3, 4-tetrahydroauinolyl, 2-oxo-1, 2, 3, 4-tetrahydroquinolyl, 2-oxo-1, 2-dihydroquinolyl, indolyl, 2-oxoindolinyl, benzothiazolyl, 2-oxobenzothiazolinyl, 3,4-dihydro-1H-2, 1-benzothiazinyl in which the S atom optionally oxidized, or 3-oxo-2, 3-dihydro-4H-1, 4-benzoxazinyl, each of which may have one or more substituentis) selected from lower alkyl. hydroxy (lower) alkyl, lower alkylamino, lower alkanoyl, cyclic lower alkanoyl, lower alkoxy (lower) alkyl, lower alkylamino (lower) alkanoyl, benzyl, benryloxy (lower)-alkyl, lower alkoxycarbonyl (lower) alkyl and 4-(2-hydroxyethyl) piperazin-1-yl-carbonylmethyl; R2 is a hydrogen, lower alkenyl, benzyl, carboxy (lower)-alkyl or lower alkoxycarbonyl (lower) alkyl; R3 and R4, which may be the same or different, are each hydrogen or lower alkyl or together represent a bond; provided that when R' is 2-oxo-1, 2,3, 4-tetrahydroquinolyl which is unsubstituted or substituted by a lower alkyl, then, R4 is a hydrogen or R2 is a lower alkenyl, benzyl, carboxy (lower) alkyl or lower alkoxycarbonyl (lower) alkyl; and pharmaceutically acceptable salt thereof, which are useful in the treatment of hypertension, thrombosis and ulcer in human beings and animals.

  由以下式子表示的新型三嗪衍生物 其中 R'是1，2，3，4-四氢金酰基、 2-氧代-1，2，3，4-四氢喹啉基、 2-氧代-1，2-二氢喹啉基 吲哚基 2-氧代吲哚啉基 苯并噻唑基 2-氧代苯并噻唑啉基、 3,4-二氢-1H-2, 1-苯并噻嗪基，其中 S 原子可选择氧化，或 3-氧代-2,3-二氢-4H-1,4-苯并恶嗪基，其中每个基团都可以有一个或多个取代基，这些取代基选自低级烷基、羟基（低级）烷基、低级烷基氨基、低级烷酰基、环状低级烷酰基、低级烷氧基（低级）烷基、低级烷氨基（低级）烷酰基、苄基、苄氧基（低级）烷基、低级烷氧基羰基（低级）烷基和 4-(2-羟乙基)烷基。 4-（2-羟乙基）哌嗪-1-基羰基甲基； R2 是氢、低级烯基、苄基、羧基（低级）烷基或低级烷氧基羰基（低级）烷基； R3和R4可以相同或不同，各自为氢或低级烷基或共同代表一个键；但当R'为未取代或被低级烷基取代的2-氧代-1，2，3，4-四氢喹啉基时，则R4为氢或R2为低级烯基、苄基、羧基（低级）烷基或低级烷氧基羰基（低级）烷基；及其药学上可接受的盐，可用于治疗人和动物的高血压、血栓和溃疡。
• US4581356A
  申请人：——

  公开号：US4581356A

  公开（公告）日：1986-04-08
• Dihydropyridazinone cardiotonics. The discovery and inotropic activity of 1,3-dihydro-3,3-dimethyl-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-indol-2-one
  作者：David W. Robertson、Joseph H. Krushinski、E. E. Beedle、V. Wyss、G. Don Pollock、Harve Wilson、Raymond F. Kauffman、J. Scott Hayes

  DOI：10.1021/jm00160a006

  日期：1986.10

  We discovered that 6 (N-[4-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)phenyl]acetamide) is a potent positive inotrope in dogs, and we have prepared several lactam analogues of this agent. These included 16 (1,3-dihydro-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-indol-2-one), 32 (the analogous quinolin-2-one), and 37 (the analogous benzazepin-2-one). The inotropic ED50's of these compounds were 24, 3.3, and 5.2 micrograms/kg, respectively, after iv administration to pentobarbital-anesthetized dogs. Compound 20 (LY195115, 1,3-dihydro-3,3-dimethyl-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-i ndol-2- one), the geminal dimethyl analogue of 16, was 3.5-fold more potent than 16 when administered iv (ED50 = 6.8 micrograms/kg). However, the most profound effect of the geminal alkyl substitution was on oral activity. The approximate ED50's of 20 and 16 after oral administration to conscious dogs were 25 and 400 micrograms/kg, respectively. The increase in contractility produced by 25 micrograms/kg of 20 was maximally sustained in excess of 8 h. Thus, 20 is one of the most potent and long-acting oral inotropes described to date.
• Triazine derivatives, and pharmaceutical compositions comprising the same
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04581356A1

  公开（公告）日：1986-04-08

  New triazine derivatives represented by the formula: ##STR1## wherein R.sup.1 is a 1,2,3,4-tetrahydroquinolyl, 2-oxo-1,2,3,4-tetrahydroquinolyl, 2-oxo-1,2-dihydroquinolyl, indolyl, 2-oxoindolinyl, benzothiazolyl, 2-oxobenzothiazolinyl, 3,4-dihydro-1H-2,1-benzothiazinyl in which the S atom being optionally oxidized, or 3-oxo-2,3-dihydro-4H-1,4-benzoxazinyl, each of which may have one or more substituent(s) selected from lower alkyl, hydroxy(lower)alkyl, lower alkylamino, lower alkanoyl, cyclic lower alkanoyl, lower alkoxy(lower)alkyl, lower alkylamino(lower)alkanoyl, benzyl, benzyloxy(lower)alkyl, lower alkoxycarbonyl(lower)alkyl and 4-(2-hydroxyethyl)piperazin-1-yl-carbonylmethyl; R.sup.2 is a hydrogen, lower alkenyl, benzyl, carboxy(lower)alkyl or lower alkoxycarbonyl(lower)alkyl; R.sup.3 and R.sup.4, which may be the same or different, are each hydrogen or lower alkyl or together represent a bond; provided that when R.sup.1 is 2-oxo-1,2,3,4-tetrahydroquinolyl which is unsubstituted or substituted by a lower alkyl, then, R.sup.4 is a hydrogen or R.sup.2 is a lower alkenyl, benzyl, carboxy(lower)alkyl or lower alkoxycarbonyl(lower)alkyl; and pharmaceutically acceptable salt thereof, which are useful in the treatment of hypertension, thrombosis and ulcer in human beings and animals.

  新的三嗪衍生物的化学式为：##STR1## 其中 R.sup.1 是1,2,3,4-四氢喹啉基、2-氧代-1,2,3,4-四氢喹啉基、2-氧代-1,2-二氢喹啉基、吲哚基、2-氧代吲哚基、苯并噻唑基、2-氧代苯并噻唑基、3,4-二氢-1H-2,1-苯并噻嗪基，其中 S 原子可选择性氧化，或者3-氧代-2,3-二氢-4H-1,4-苯并噁嗪基，每个基可能有一个或多个取代基，所选自较低烷基、羟基(较低)烷基、较低烷基氨基、较低烷酰基、环状较低烷酰基、较低烷氧(较低)烷基、较低烷基氨基(较低)烷酰基、苄基、苄氧(较低)烷基、较低烷氧羰基(较低)烷基和4-(2-羟乙基)哌嗪-1-基羰基甲基；R.sup.2 是氢、较低烯基、苄基、羧基(较低)烷基或较低烷氧羰基(较低)烷基；R.sup.3 和 R.sup.4，可能相同也可能不同，分别是氢或较低烷基，或者一起表示一个键；但是当 R.sup.1 是未取代或被较低烷基取代的2-氧代-1,2,3,4-四氢喹啉基时，那么 R.sup.4 是氢或 R.sup.2 是较低烯基、苄基、羧基(较低)烷基或较低烷氧羰基(较低)烷基；以及其药学上可接受的盐，用于治疗人类和动物的高血压、血栓形成和溃疡。