3-[(4-甲基喹啉-2-基)氨基]-3-氧代丙酸乙酯 | 168425-49-8

• 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: 3-[(4-甲基喹啉-2-基)氨基]-3-氧代丙酸乙酯
• 英文名称: ethyl N-(4-methyl-2-quinolinyl)malonamate
• 英文别名: Ethyl (4-methylquinolin-2-yl)carbamoylacetate；Propanoic acid, 3-[(4-methyl-2-quinolinyl)amino]-3-oxo-, ethyl ester；ethyl 3-[(4-methylquinolin-2-yl)amino]-3-oxopropanoate
• CAS: 168425-49-8
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: VIHLJBYGKFVMIG-UHFFFAOYSA-N

物化性质

• 沸点：
  492.7±35.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(4-甲基喹啉-2-基)氨基]-3-氧代丙酸乙酯 在 PPA 、 三氯氧磷 作用下， 反应 3.0h， 以64%的产率得到3-chloro-6-methyl-1H-pyrimido<1,2-a>quinolin-1-one
  参考文献：
  名称：

  1,2-Fused pyrimidines VII. 3-(Dialkylamino)-1H-pyrimido[1,2-a]quinolin-1-ones and 2-(dialkylamino)-4H-pyrimido[2,1-a]isoquinolin-4-ones as antiplatelet compounds

  摘要：

  A number of 3-(dialkylamino)-1H-pyrimido[1,2-a]quinolin-1 ones 3 and 2-(dialkylamino)-4H-pyrimido [2,1-a]isoquinolin-4-ones 4 were prepared by treating the corresponding chloro derivatives with an excess of dialkylamines. The highest in vitro antiplatelet activity was obtained when the dialkylamino substituent was 1-piperazinyl (compounds 3g and 4e). The novel 2-(1-piperazinyl)-4H-pyrido[ ,2-a]pyrimidin-4-one 2a was also prepared by an analogous procedure, which resulted in the most active compound towards all the platelet aggregation inducers used (ADP, collagen, A 23187). Moreover, some examples of 1-(dialkylamino)-3H pyrimido[l,2-a]quinolin-3-ones 5 and 4-(dialkylamino)-2H-pyrimido[2,1-a]isoquinolin-2-ones 6 were also obtained (together with negligible or lower amounts of the corresponding isomers 3 and 4, respectively) from the cyclocondensation of the appropriate ethyl N,N-dialkylmalonamate/phosphorus oxychloride reagents 13 with 2-aminoquinoline or 1-aminoisoquinoline. These;latter compounds showed a rather low antiplatelet activity.

  DOI：

  10.1016/0223-5234(96)88206-7
• 作为产物：
  描述：

  4-甲基-2-喹啉胺 、 氯甲酰乙酸乙酯 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以60%的产率得到3-[(4-甲基喹啉-2-基)氨基]-3-氧代丙酸乙酯
  参考文献：
  名称：

  1,2-Fused pyrimidines VII. 3-(Dialkylamino)-1H-pyrimido[1,2-a]quinolin-1-ones and 2-(dialkylamino)-4H-pyrimido[2,1-a]isoquinolin-4-ones as antiplatelet compounds

  摘要：

  A number of 3-(dialkylamino)-1H-pyrimido[1,2-a]quinolin-1 ones 3 and 2-(dialkylamino)-4H-pyrimido [2,1-a]isoquinolin-4-ones 4 were prepared by treating the corresponding chloro derivatives with an excess of dialkylamines. The highest in vitro antiplatelet activity was obtained when the dialkylamino substituent was 1-piperazinyl (compounds 3g and 4e). The novel 2-(1-piperazinyl)-4H-pyrido[ ,2-a]pyrimidin-4-one 2a was also prepared by an analogous procedure, which resulted in the most active compound towards all the platelet aggregation inducers used (ADP, collagen, A 23187). Moreover, some examples of 1-(dialkylamino)-3H pyrimido[l,2-a]quinolin-3-ones 5 and 4-(dialkylamino)-2H-pyrimido[2,1-a]isoquinolin-2-ones 6 were also obtained (together with negligible or lower amounts of the corresponding isomers 3 and 4, respectively) from the cyclocondensation of the appropriate ethyl N,N-dialkylmalonamate/phosphorus oxychloride reagents 13 with 2-aminoquinoline or 1-aminoisoquinoline. These;latter compounds showed a rather low antiplatelet activity.

  DOI：

  10.1016/0223-5234(96)88206-7

文献信息

• The Chemistry of 5-Oxodihydroisoxasoles. XIV. Synthesis of 2-(1-Aryltetrazol-5-yl)propanoic Acids
  作者：D Caiazza、RH Prager、K Schafer

  DOI：10.1071/ch9951861

  日期：——

  A number of N-arylisoxazol-5(2H)-ones (aryl = phenyl, isoquinolin-1-yl, quinolin-2-yl, 2-phenylquinazolin-4-yl and benzothiazol-2-yl) have been reacted with lithium azide to give 2-(1-aryltetrazol-5-yl)acetic esters, which have been C- methylated and hydrolysed. The resulting 2-(1-aryltetrazol-5-yl) propanoic acids had low antiinflammatory activity, as judged by inhibition of synthesis of prostaglandin PGE2 or tumour necrosis factor α.

  一些 N-芳基异恶唑-5(2H)-酮（芳基=苯基、异喹啉-1-基、喹啉-2-基、2-苯基喹唑啉-4-基和苯并噻唑-2-基）与叠氮化锂反应生成 2-(1-芳基四唑-5-基)乙酸酯，这些酯经过 C-甲基化和水解。根据对前列腺素 PGE2 或肿瘤坏死因子 α 合成的抑制作用判断，生成的 2-(1-芳基四唑-5-基)丙酸的抗炎活性较低。
• 1,2-Fused pyrimidines VII. 3-(Dialkylamino)-1H-pyrimido[1,2-a]quinolin-1-ones and 2-(dialkylamino)-4H-pyrimido[2,1-a]isoquinolin-4-ones as antiplatelet compounds
  作者：M Di Braccio、G Roma、G Leoncini

  DOI：10.1016/0223-5234(96)88206-7

  日期：1995.1

  A number of 3-(dialkylamino)-1H-pyrimido[1,2-a]quinolin-1 ones 3 and 2-(dialkylamino)-4H-pyrimido [2,1-a]isoquinolin-4-ones 4 were prepared by treating the corresponding chloro derivatives with an excess of dialkylamines. The highest in vitro antiplatelet activity was obtained when the dialkylamino substituent was 1-piperazinyl (compounds 3g and 4e). The novel 2-(1-piperazinyl)-4H-pyrido[ ,2-a]pyrimidin-4-one 2a was also prepared by an analogous procedure, which resulted in the most active compound towards all the platelet aggregation inducers used (ADP, collagen, A 23187). Moreover, some examples of 1-(dialkylamino)-3H pyrimido[l,2-a]quinolin-3-ones 5 and 4-(dialkylamino)-2H-pyrimido[2,1-a]isoquinolin-2-ones 6 were also obtained (together with negligible or lower amounts of the corresponding isomers 3 and 4, respectively) from the cyclocondensation of the appropriate ethyl N,N-dialkylmalonamate/phosphorus oxychloride reagents 13 with 2-aminoquinoline or 1-aminoisoquinoline. These;latter compounds showed a rather low antiplatelet activity.