4H-imidazo<2,1-c><1,4>benzoxazine-2-carboxylic acid | 65565-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4H-imidazo<2,1-c><1,4>benzoxazine-2-carboxylic acid
• 英文别名: 4H-Imidazo<2,1-c><1,4>benzoxazin-2-carbonsaeure；4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylic acid；4H-benzo[b]imidazo[1,2-d][1,4]oxazine-2-carboxylic acid；4H-imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid
• CAS: 65565-73-3
• 化学式: C₁₁H₈N₂O₃
• 分子量: 216.196
• InChiKey: VVHVOAHQUDZCMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4H-imidazo<2,1-c><1,4>benzoxazine-2-carboxylic acid 反应 0.17h， 以88%的产率得到4H-imidazo<2,1-c><1,4>benzoxazine
  参考文献：
  名称：

  Danswan, Geoff W.; Hairsine, Peter W.; Rowlands, David A., Journal of the Chemical Society. Perkin transactions I, 1982, p. 1049 - 1058

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-(chloroacetamido)-2-<2-oxo-2H-1,4-benzoxazin-3-yl>acetate 在 盐酸 、 sodium hydroxide 、 水 、 sodium carbonate 、 丙酮 作用下， 以 甲醇 为溶剂， 反应 2.58h， 生成 4H-imidazo<2,1-c><1,4>benzoxazine-2-carboxylic acid
  参考文献：
  名称：

  Danswan, Geoff W.; Hairsine, Peter W.; Rowlands, David A., Journal of the Chemical Society. Perkin transactions I, 1982, p. 1049 - 1058

  摘要：

  DOI：

文献信息

• Novel imidazobenzoxazines
  申请人：Roussel Uclaf

  公开号：US04145419A1

  公开（公告）日：1979-03-20

  Novel imidazobenzoxazines of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, nitro, NH.sub.2 and a protected amino Z is selected from the group consisting of --COOR, and ##STR2## R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, ##STR3## alkali metal, alkaline earth metal, magnesium, aluminum and nitrogen bases, n is 1,2 or 3, R.sub.1 and R.sub.2 individually are selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and taken together with the nitrogen atom to which they are attached form a saturated heterocyclic ring of 4 to 6 carbon atoms optionally interrupted by another heteroatom which may optionally be substituted with alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antiallergic and bronchodilatory activity and their preparation.

  新型咪唑苯并噁嗪的化学式为##STR1##，其中X从氢、硝基、NH.sub.2和受保护的氨基Z中选择，Z从--COOR和##STR2##中选择，R从氢、1至5个碳原子的烷基、##STR3##碱金属、碱土金属、镁、铝和氮碱中选择，n为1、2或3，R.sub.1和R.sub.2分别从氢和1至5个碳原子的烷基中选择，并与它们连接的氮原子一起形成由另一个杂原子中断的4至6个碳原子的饱和杂环，该杂原子可选择性地用1至5个碳原子的烷基替代，并具有抗过敏和支气管扩张活性的非毒性、药用可接受的酸盐及其制备。
• 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.
• DANSWAN, G. W.;HAIRSINE, P. W.;ROWLANDS, D. A.;TAYLOR, J. B.;WESTWOOD, R., J. CHEM. SOC. PERKIN TRANS., 1982, N 4, 1049-1058
  作者：DANSWAN, G. W.、HAIRSINE, P. W.、ROWLANDS, D. A.、TAYLOR, J. B.、WESTWOOD, R.

  DOI：——

  日期：——
• 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：——
• US4145419A
  申请人：——

  公开号：US4145419A

  公开（公告）日：1979-03-20