(3,4-dihydro-2H-quinolin-1-yl)-oxo-acetic acid ethyl ester | 14164-86-4

• 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: (3,4-dihydro-2H-quinolin-1-yl)-oxo-acetic acid ethyl ester
• 英文别名: 3-(3,4-dihydro-2H-quinolin-1-yl)-2-oxopropionic acid ethyl ester；N-Ethoxalyl-1,2,3,4-tetrahydroquinoline；N-Ethoxalyl-1,2,3,4-tetrahydrochinolin；ethyl 2-(3,4-dihydro-2H-quinolin-1-yl)-2-oxoacetate
• CAS: 14164-86-4
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: VKNITXPXVPYYKI-UHFFFAOYSA-N

物化性质

• 熔点：
  187-189 °C
• 沸点：
  187-189 °C(Press: 8 Torr)
• 密度：
  1.1099 g/cm3(Temp: 21 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,4-dihydro-2H-quinolin-1-yl)-oxo-acetic acid ethyl ester 在 magnesium chloride 作用下， 以 四氢呋喃 、 乙二醇甲醚 为溶剂， 反应 6.0h， 以48%的产率得到5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-羧酸乙酯
  参考文献：
  名称：

  Agents and methods for the treatment of proliferative diseases

  摘要：

  这项发明提供了式（I）的选择性激酶抑制剂。

  公开号：

  US20030229026A1
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉 、 3-溴丙酮酸乙酯 以 四氢呋喃 为溶剂， 反应 24.5h， 生成 (3,4-dihydro-2H-quinolin-1-yl)-oxo-acetic acid ethyl ester
  参考文献：
  名称：

  Agents and methods for the treatment of proliferative diseases

  摘要：

  这项发明提供了式（I）的选择性激酶抑制剂。

  公开号：

  US20030229026A1

文献信息

• Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor
  作者：Ryu Nagata、Norihiko Tanno、Toru Kodo、Nobuyuki Ae、Hiroshi Yamaguchi、Tamiki Nishimura、Fujio Antoku、Tohru Tatsuno、Terufumi Kato

  DOI：10.1021/jm00049a015

  日期：1994.11

  A series of tricyclic quinoxalinediones, 5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones, were synthesized and was evaluated for their affinity for the glycine binding site of the NMDA receptor using a [H-3]- 5,7-dichlorokynurenic acid binding assay. The six-membered ring-fused tricyclic quinoxalinedione 18g (K-i = 9.9 nM) displayed high affinity for the glycine site. The anilide derivative 20g (K-i = 2.6 nM) was 4-fold more potent than 18g and as potent as L-689,560, one of the most potent glycine antagonists so far prepared. Although the carboxylic acid derivative of the corresponding five-membered ring-fused tricyclic quinoxalinedione 18e (K-i = 7.3 nM) had affinity comparable to that of 18g, the anilide derivative 20e largely decreased in the affinity in contrast to 20g. Enantiomers 23g, 24g, 25g, and 26g were prepared and tested. Only the S enantiomer 25g (K-i = 0.96 nM) retained the affinity among the anilide derivatives, whereas both enantiomers 23g (K-i = 2.3 nM) and 24g (K-i = 9.6 nM) were active among the carboxylic acid derivatives. The origin of the high affinity of carboxylic acid derivatives such as 18e and 18g would be a charge-charge interaction between the anionic carboxylate residues of the compounds and the cationic proton-donor site in the receptor.
• TRICYCLIC QUINOXALINEDIONES AS GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0642508A1

  公开（公告）日：1995-03-15
• Agents and methods for the treatment of proliferative diseases
  申请人：——

  公开号：US20030229026A1

  公开（公告）日：2003-12-11

  The present invention provides selective kinase inhibitors of formula (I). 1

  这项发明提供了式（I）的选择性激酶抑制剂。