(4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-10-yl)glycolic acid | 173155-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]吡嗪-8-酮
• 英文名称: (4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-10-yl)glycolic acid
• 英文别名: 10-(1-carboxy-1-hydroxymethyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one；(4,5-dihydro-4-oxo-10H-imidazo(1,2-a]indeno[1,2-e]pyrazin-10-yl)glycolic acid；2-hydroxy-2-(7-oxo-2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10,12,14-hexaen-16-yl)acetic acid
• CAS: 173155-72-1
• 化学式: C₁₅H₁₁N₃O₄
• 分子量: 297.27
• InChiKey: DNQQOSSJASAJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-10-yl)glycolic acid 在 盐酸 、 硫酸 、 乙酸酐 、 铁粉 、 potassium nitrate 、 zinc(II) chloride 作用下， 生成 methyl (8-amino-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetate
  参考文献：
  名称：

  8-Methylureido-4,5-dihydro-4-oxo-10 H -imidazo[1,2- a ]indeno-[1,2- e ]pyrazines: highly potent in vivo AMPA antagonists

  摘要：

  A novel series of readily water soluble 8-methylureido-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazines were synthesized. The -10-yl acetic acid ((+)-3) and -10-carboxylidene (4) derivatives exhibit potent affinities (IC50 = 4 and 19 nM, respectively) and antagonist properties (IC50 = 2 and 3 nM, respectively) at the ionotropic AMPA receptor. These compounds also display anticonvulsant properties against both electrically and sound-induced convulsions in mice after ip, sc and iv administration with ED50 values between 0.9 and 11 mg/kg, thus suggesting adequate brain penetration. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00054-8
• 作为产物：
  描述：

  乙醛酸 、 5H,10H-imidazo<1,2-a>indeno<1,2-e>pyrazin-4-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到(4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-10-yl)glycolic acid
  参考文献：
  名称：

  8-Methylureido-4,5-dihydro-4-oxo-10 H -imidazo[1,2- a ]indeno-[1,2- e ]pyrazines: highly potent in vivo AMPA antagonists

  摘要：

  A novel series of readily water soluble 8-methylureido-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazines were synthesized. The -10-yl acetic acid ((+)-3) and -10-carboxylidene (4) derivatives exhibit potent affinities (IC50 = 4 and 19 nM, respectively) and antagonist properties (IC50 = 2 and 3 nM, respectively) at the ionotropic AMPA receptor. These compounds also display anticonvulsant properties against both electrically and sound-induced convulsions in mice after ip, sc and iv administration with ED50 values between 0.9 and 11 mg/kg, thus suggesting adequate brain penetration. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00054-8

文献信息

• Imidazo (1,2-A)-Indeno (1,2-E) pyrazin-4-one derivatives and
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05807859A1

  公开（公告）日：1998-09-15

  Pharmaceutical compositions containing, as the active principle, compounds of formula (I): ##STR1## wherein R, R.sub.1 and R.sub.2 are as defined in the description, or salts thereof, the novel compounds of formula (I), and the preparation thereof. The compounds of formula (I) have valuable pharmacological properties and are alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, this receptor also being known as the quisqualate receptor. Furthermore, the compounds of formula (I) are non-competitive N-methyl-D-aspartate (NDMA) receptor antagonists, and particularly NMDA receptor glycine modulation site ligands.

  含有作为活性原理的化合物的药物组合物，其化学式为(I)：##STR1##其中R、R.sub.1和R.sub.2如描述中所定义，或其盐，化学式(I)的新化合物及其制备方法。化学式(I)的化合物具有有价值的药理特性，是α-氨基-3-羟基-5-甲基-4-异恶唑丙酸（AMPA）受体拮抗剂，该受体也被称为喹氨酸受体。此外，化学式(I)的化合物是非竞争性N-甲基-D-天冬氨酸（NDMA）受体拮抗剂，特别是NMDA受体甘氨酸调节位点配体。
• DERIVES D'IMIDAZO[1,2-a]INDENO[1,2-e]PYRAZIN-4-ONE ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：Aventis Pharma S.A.

  公开号：EP0752992B1

  公开（公告）日：2001-05-30
• US5807859A
  申请人：——

  公开号：US5807859A

  公开（公告）日：1998-09-15
• 8-Methylureido-4,5-dihydro-4-oxo-10 H -imidazo[1,2- a ]indeno-[1,2- e ]pyrazines: highly potent in vivo AMPA antagonists
  作者：Serge Mignani、Georg Andrees Bohme、Alain Boireau、Michel Cheve、Dominique Damour、Marc-Williams Debono、Arielle Genevois-Borella、Assunta Imperato、Patrick Jimonet、Jeremy Pratt、John C.R. Randle、Yves Ribeill、Marc Vuilhorgne、Jean-Marie Stutzmann

  DOI：10.1016/s0960-894x(00)00054-8

  日期：2000.3

  A novel series of readily water soluble 8-methylureido-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazines were synthesized. The -10-yl acetic acid ((+)-3) and -10-carboxylidene (4) derivatives exhibit potent affinities (IC50 = 4 and 19 nM, respectively) and antagonist properties (IC50 = 2 and 3 nM, respectively) at the ionotropic AMPA receptor. These compounds also display anticonvulsant properties against both electrically and sound-induced convulsions in mice after ip, sc and iv administration with ED50 values between 0.9 and 11 mg/kg, thus suggesting adequate brain penetration. (C) 2000 Elsevier Science Ltd. All rights reserved.