ethyl 4,5-dihydro-4-oxoimidazo<1,2-a>quinoxaline-2-carboxylate | 76002-83-0

• 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: ethyl 4,5-dihydro-4-oxoimidazo<1,2-a>quinoxaline-2-carboxylate
• 英文别名: Ethyl 4,5-dihydro-4-oxo-imidazo<1,2-a>quinoxalin-2-carboxylate；ethyl 4,5-dihydro-4-oxoimidazo-[1,2-a]-quinoxaline-2-carboxylate；ethyl 4(5H)-oxoimidazo-[1,2-a]-quinoxaline-2-carboxylate；ethyl 4-oxo-5H-imidazo[1,2-a]quinoxaline-2-carboxylate
• CAS: 76002-83-0
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: CVUSRNRRQQKZPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  292-293 °C(Solv: ethanol (64-17-5))
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4,5-dihydro-4-oxoimidazo<1,2-a>quinoxaline-2-carboxylate 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 4,5-dihydro-5-ethyl-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
• 作为产物：
  描述：

  2-氨基-3-氯喹喔啉 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 2.0h， 生成 ethyl 4,5-dihydro-4-oxoimidazo<1,2-a>quinoxaline-2-carboxylate
  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。
• 一类toll样受体调节剂、其药物组合物、制备方 法与用途
  申请人：北京施安泰医药技术开发有限公司

  公开号：CN108794485B

  公开（公告）日：2020-04-24

  本发明属于药物化学领域，具体涉及一类具有toll样受体调节作用的化合物、其制备方法及用途。本发明提供如下式X所示的化合物。式X化合物可用作toll样受体调节剂，其活性较高。此外，本发明化合物具有高效低毒、抗耐药性等特点，具有临床应用价值。并且，本发明化合物合成步骤简单，因此具备较大的经济利用价值。
• 一种喹喔啉类衍生物的制备方法
  申请人：上海睿智化学研究有限公司

  公开号：CN117384164A

  公开（公告）日：2024-01-12

  本发明公开了一种喹喔啉类衍生物的制备方法。本发明提供的制备方法，其包括如下步骤：在溶剂中，将如式I所示的化合物和3‑溴‑2‑氧代丙酸乙酯进行如下所示的反应，得到如式II所示的化合物。该制备方法具有收率高、产物纯度高、成本较低、操作简便等优点。#imgabs0#
• HETEROCYCLIC COMPOUNDS AND THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0743945B1

  公开（公告）日：2002-03-06
• 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：——