5-methyl-4-oxo-4,5-dihydro-pyrrolo[1,2-a]quinoxaline-2-carboxylic acid ethyl ester | 69015-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-methyl-4-oxo-4,5-dihydro-pyrrolo[1,2-a]quinoxaline-2-carboxylic acid ethyl ester
• 英文别名: ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylate；ethyl 5-methyl-4-oxopyrrolo[1,2-a]quinoxaline-2-carboxylate
• CAS: 69015-14-1
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: PZWQSMRYBZVRPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-4-oxo-4,5-dihydro-pyrrolo[1,2-a]quinoxaline-2-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到5-methyl-4-oxo-4,5-dihydro-pyrrolo[1,2-a]quinoxaline-2-carboxylic acid
  参考文献：
  名称：

  Pyrroloquinoxalines

  摘要：

  该专利描述了一种新型吡咯喹喔啉类化合物，化学结构如下：其中X和Y分别选自氢、卤素、1至5个碳原子的烷基和烷氧基以及--NO.sub.2的组合，Z选自1至8个碳原子的烷基、3至8个碳原子的环烷基、2至6个碳原子的烯基和苯基，R选自氢、1至5个碳原子的烷基、以及非毒性、药学上可接受的阳离子，n是1至6的整数，R.sub.1和R.sub.2分别为1至5个碳原子的烷基，以及具有抗过敏活性的非毒性、药学上可接受的酸盐，以及其制备的新方法。

  公开号：

  US04151280A1
• 作为产物：
  描述：

  1-甲基苯并咪唑 在 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成 5-methyl-4-oxo-4,5-dihydro-pyrrolo[1,2-a]quinoxaline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009

文献信息

• Pyrroloquinoxalines
  申请人：Roussel Uclaf

  公开号：US04151280A1

  公开（公告）日：1979-04-24

  Novel pyrroloquinoxalines of the formula ##STR1## wherein X and Y are individually selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms and --NO.sub.2, Z is selected from the group consisting of alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms and phenyl and R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, ##STR2## and non-toxic, pharmaceutically acceptable cations, n is an integer from 1 to 6 and R.sub.1 and R.sub.2 are individually alkyl of 1 to 5 carbon atoms and the non-toxic, pharmaceutically acceptable acid addition salts thereof having antiallergic activity and to a novel process for their preparation.

  该专利描述了一种新型吡咯喹喔啉类化合物，化学结构如下：其中X和Y分别选自氢、卤素、1至5个碳原子的烷基和烷氧基以及--NO.sub.2的组合，Z选自1至8个碳原子的烷基、3至8个碳原子的环烷基、2至6个碳原子的烯基和苯基，R选自氢、1至5个碳原子的烷基、以及非毒性、药学上可接受的阳离子，n是1至6的整数，R.sub.1和R.sub.2分别为1至5个碳原子的烷基，以及具有抗过敏活性的非毒性、药学上可接受的酸盐，以及其制备的新方法。
• AGER, IAN R.;BARNES, ALAN C.;DANSWAN, GEOFFREY W.;HAIRSINE, PETER W.;KAY,+, J. MED. CHEM., 31,(1988) N 6, 1098-1115
  作者：AGER, IAN R.、BARNES, ALAN C.、DANSWAN, GEOFFREY W.、HAIRSINE, PETER W.、KAY,+

  DOI：——

  日期：——
• US4151280A
  申请人：——

  公开号：US4151280A

  公开（公告）日：1979-04-24
• Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles
  作者：Ian R. Ager、Alan C. Barnes、Geoffrey W. Danswan、Peter W. Hairsine、David P. Kay、Peter D. Kennewell、Saroop S. Matharu、Peter Miller、Peter Robson

  DOI：10.1021/jm00401a009

  日期：1988.6

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.