1-benzoyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester | 21203-33-8

• 分子结构分类: 有机化合物
• 英文名称: 1-benzoyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester
• 英文别名: 3-ethoxycarbonyl-1-benzoyl-4H-quinolizin-4-one；1-Benzoyl-3-ethoxycarbonyl-4-oxo-4H-chinolizin；ethyl 1-benzoyl-4-oxoquinolizine-3-carboxylate
• CAS: 21203-33-8
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: MOLYZNZCFPRIQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzoyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester 在 乙醇 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 1-benzoyl-4-oxo-4H-quinolizine-3-carboxylic acid
  参考文献：
  名称：

  Quinolizidinone Carboxylic Acids as CNS Penetrant, Selective M₁ Allosteric Muscarinic Receptor Modulators

  摘要：

  Positive allosteric modulation of the M, muscarinic receptor represents an approach to treat the cognitive decline in patients with Alzheimer's disease. Replacement of a quinolone ring system in a quinolone carboxylic acid series of M, modulators with a quinolizidinone bearing a basic amine linkage led to a series of compounds with higher free fraction, enhanced CNS exposure, and improved efficacy in rodent in vivo models of cognition.

  DOI：

  10.1021/ml100095k
• 作为产物：
  描述：

  ethyl 1-[hydroxy(phenyl)methyl]-4-oxo-4H-quinolizine-3-carboxylate 在 2-碘酰基苯甲酸 作用下， 以 乙腈 为溶剂， 生成 1-benzoyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Quinolizidinone Carboxylic Acids as CNS Penetrant, Selective M₁ Allosteric Muscarinic Receptor Modulators

  摘要：

  Positive allosteric modulation of the M, muscarinic receptor represents an approach to treat the cognitive decline in patients with Alzheimer's disease. Replacement of a quinolone ring system in a quinolone carboxylic acid series of M, modulators with a quinolizidinone bearing a basic amine linkage led to a series of compounds with higher free fraction, enhanced CNS exposure, and improved efficacy in rodent in vivo models of cognition.

  DOI：

  10.1021/ml100095k

文献信息

• Quinolizinone compounds and pharmaceutical composition comprising the
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04650804A1

  公开（公告）日：1987-03-17

  The invention relates to novel quinolizinone compounds having inhibitory activity on allergies and ulcers, of the formula: ##STR1## wherein R.sup.1 is tetrazolylcarbamoyl; R.sup.7 is hydrogen or aryl selected from phenyl, tolyl, xylyl, cumenyl, naphthyl and biphenylyl; R.sup.2 is hydrogen, hydroxy, lower alkyl or lower alkoxy; R.sup.3 is hydrogen, hydroxy, lower alkyl, lower alkoxy, lower alkenyloxy, phenyl, napthyl, biphenylyl, phenyl having one or more substituent(s) selected from halogen, lower alkyl and lower alkoxy, arylthio selected from phenylthio, tolylthio, xylylthio, cumenylthio, naphthylthio and biphenylthio, aroyl selected from benzoyl, toluoyl and naphthoyl, ar(lower)alkyl selected from phenyl(lower)alkyl, tolyl(lower)alkyl, xylyl(lower)alkyl, cumenyl(lower)alkyl, naphthyl(lower)alkyl and biphenylyl(lower)alkyl, arenesulfonyl selected from benzenesulfonyl and p-toluenesulfonyl, arylamino selected from phenylamino, naphthylamino, biphenylylamino, phenylamino having lower alkyl on the nitrogen atom or aryloxy selected from phenoxy and tolyloxy; or pharmaceutically acceptable salts thereof.

  该发明涉及一种具有对过敏和溃疡具有抑制活性的新型喹诺利酮化合物，其化学式为：其中R.sup.1为四唑基甲酰基；R.sup.7为氢或苯基，所述苯基选自苯基、甲苯基、二甲苯基、辛基、萘基和联苯基；R.sup.2为氢、羟基、低碳基或低烷氧基；R.sup.3为氢、羟基、低碳基、低烷氧基、低烯烷氧基、苯基、萘基、联苯基、苯基具有一个或多个取代基所选自卤素、低烷基和低烷氧基、芳基硫基所选自苯硫基、甲苯硫基、二甲苯硫基、辛基硫基、萘硫基和联苯硫基、芳酰基所选自苯甲酰基、甲苯甲酰基和萘甲酰基、芳基烷基所选自苯基烷基、甲苯基烷基、二甲苯基烷基、辛基烷基、萘基烷基和联苯基烷基、芳基磺酰基所选自苯磺酰基和对甲苯磺酰基、芳基氨基所选自苯氨基、萘氨基、联苯基氨基、苯氨基氮原子上具有低碳基或芳氧基所选自苯氧基和甲苯氧基；或其药学上可接受的盐。
• Quinolizinone compounds, and pharmaceutical composition comprising the
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04698349A1

  公开（公告）日：1987-10-06

  The invention relates to novel quinolizinone compounds, of inhibitory activity on allergies and ulcers, of the formula: ##STR1## wherein R.sup.1 is carboxy, carbamoyl Y.sup.1, phenylcarbamoyl which may have hydroxy, cyano or thiocarbamoyl, R.sup.7 is hydrogen or aryl selected from phenyl, tolyl, xylyl, cumenyl, naphthyl and biphenylyl; R.sup.2 is hydrogen, hydroxy, lower alkyl or lower alkoxy; and R.sup.3 is hydrogen, hydroxy, lower alkyl, lower alkoxy, lower alkenyloxy, phenyl, naphthyl, biphenylyl, phenyl having one or more substituent(s) selected from halogen, lower alkyl and lower alkoxy, arylthio selected from phenylthio, tolylthio, xylylthio, cumenylthio, naphthylthio and biphenylylthio, aroyl selected from benzoyl, toluoyl and naphthoyl, ar(lower)alkyl selected from phenyl(lower)alkyl, tolyl(lower)alkyl, xylyl(lower)alkyl, cumenyl(lower)alkyl, naphthyl(lower)alkyl and biphenylyl(lower)alkyl, arenesulfonyl selected from benzenesulfonyl and p-toluenesulfonyl, arylamino selected from phenylamino, naphthylamino, biphenylylamino, phenylamino having lower alkyl on the nitrogen atom or aryloxy selected from phenoxy and tolyloxy; or pharmaceutically acceptable salts thereof.

  本发明涉及一种新的喹诺啉酮化合物，具有抗过敏和抗溃疡的抑制活性，其化学式为：##STR1## 其中，R.sup.1为羧基，氨基甲酰Y.sup.1，苯基氨基甲酰，可以具有羟基、氰基或硫代氨基甲酰基；R.sup.7为氢或被选自苯基、甲苯基、二甲苯基、叔丁基苯基、萘基和联苯基的芳基；R.sup.2为氢、羟基、低碳基或低碳氧基；R.sup.3为氢、羟基、低碳基、低碳氧基、低碳烯氧基、苯基、萘基、联苯基、苯基上有一个或多个卤素、低碳基和低碳氧基的取代基、芳基硫取代基，被选自苯基硫、甲苯基硫、二甲苯基硫、叔丁基苯基硫、萘基硫和联苯基硫、芳基酰基，被选自苯甲酰基、甲苯甲酰基和萘甲酰基、芳基（低）烷基，被选自苯基（低）烷基、甲苯基（低）烷基、二甲苯基（低）烷基、叔丁基苯基（低）烷基、萘基（低）烷基和联苯基（低）烷基、芳基磺酰基，被选自苯磺酰基和对甲苯磺酰基、芳基氨基，被选自苯基氨基、萘基氨基、联苯基氨基、氮原子上带有低碳基的苯基氨基或被选自苯氧基和甲苯氧基的芳氧基；或其药学上可接受的盐。
• Quinolizinone compound, processes for preparation thereof and pharmaceutical composition comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0157346B1

  公开（公告）日：1990-01-31
• US4650804A
  申请人：——

  公开号：US4650804A

  公开（公告）日：1987-03-17
• US4698349A
  申请人：——

  公开号：US4698349A

  公开（公告）日：1987-10-06