4,5-dihydro-5-propyl-4-oxoimidazo-[1,2-a]-quinoxaline-2-carboxylic acid | 76325-52-5

• 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: 4,5-dihydro-5-propyl-4-oxoimidazo-[1,2-a]-quinoxaline-2-carboxylic acid
• 英文别名: 4-Oxo-5-propylimidazo[1,2-a]quinoxaline-2-carboxylic acid
• CAS: 76325-52-5
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: FSSOBRKFAJWSCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-3-氯喹喔啉 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4,5-dihydro-5-propyl-4-oxoimidazo-[1,2-a]-quinoxaline-2-carboxylic acid
  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

• Oxoimidazoquinoxalines
  申请人：Roussel Uclaf

  公开号：US04291033A1

  公开（公告）日：1981-09-22

  Novel oxoimidazoquinoxalines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, chlorine and bromine, X is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms and cycloalkyl-alkyl of 4 to 6 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen alkyl of 1 to 5 carbon atoms, alkali metal, alkaline earth metal, aluminum, --NH.sub.4, organic amine and ##STR2## R.sub.4 and R.sub.5 are individually alkyl of 1 to 5 carbon atoms or taken together with the nitrogen atom form a saturated heterocycle of 4 to 6 carbon atoms optionally containing an oxygen atom or second nitrogen atom and n is a number from 1 to 5 and their non-toxic, pharmaceutically acceptable acid addition salts having antiallergic activity and their preparation.

  化合物oxoimidazoquinoxalines的结构式如下：##STR1## 其中R.sub.1和R.sub.2分别从氢、氯和溴中选择，X从1到5个碳原子的烷基、3到5个碳原子的环烷基和4到6个碳原子的环烷基-烷基中选择，R.sub.3从1到5个碳原子的烷基、碱金属、碱土金属、铝、--NH.sub.4、有机胺和##STR2##中选择，R.sub.4和R.sub.5分别是1到5个碳原子的烷基，或与氮原子一起形成4到6个碳原子的饱和杂环，可选含氧或第二个氮原子，n是1到5的数字。它们的无毒，药学可接受的酸盐具有抗过敏活性，并且可以制备这些酸盐。
• 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：——
• US4291033A
  申请人：——

  公开号：US4291033A

  公开（公告）日：1981-09-22