8-nitro-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one | 156484-27-4

• 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: 8-nitro-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
• 英文别名: 5H,10H-8-nitroimidazo[1,2-a]indeno[1,2-e]pyrazine-4-one；5H,10H-8-nitroimidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one；13-nitro-2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10(15),11,13-hexaen-7-one
• CAS: 156484-27-4
• 化学式: C₁₃H₈N₄O₃
• 分子量: 268.232
• InChiKey: FTWWNFYQSPXDJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-nitro-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 20.0 ℃ 、120.0 kPa 条件下， 生成 8-Amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one
  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：

  5H,10H-imidazo<1,2-a>indeno<1,2-e>pyrazin-4-one 在 硫酸 、 potassium nitrate 作用下， 生成 8-nitro-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
  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。
• Indeno\x9b1,2-E!pyrazine-4-ones, their preparation and the medicaments
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05789406A1

  公开（公告）日：1998-08-04

  The compounds of formula (I) ##STR1## wherein R, R.sub.1 and R.sub.2 are defined in the disclosure, and salts thereof. The compounds of formula (I) are non-competitive N-methyl-D-asparate (NMDA) receptor antagonists, particularly NMDA receptor glycine modulation site ligands, and are alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, this receptor is also known as the quisqualate receptor.

  式(I)的化合物##STR1##其中R、R.sub.1和R.sub.2在披露中有定义，并其盐。式(I)的化合物是非竞争性N-甲基-D-天冬氨酸(NMDA)受体拮抗剂，特别是NMDA受体甘氨酸调节位点配体，并且是α-氨基-3-羟基-5-甲基-4-异恶唑丙酸(AMPA)受体拮抗剂，这种受体也被称为喹氯酸受体。
• Derivatives of 5H, 10H-imidazo\x9b1, 2-a!indeno\x9b1,2-e!pyrazin-4-one,
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05677306A1

  公开（公告）日：1997-10-14

  Compounds having the formula (I) wherein R and R.sub.1, similar or different, represent a hydrogen or halogen atom or a radical alkyl, alkoxy, amino, acylamino, phenylureido, --N.dbd.CH--N(R.sub.2)R.sub.3, nitro, imidazolyl, phenyl, SO.sub.3 H or cyano; R.sub.2 and R.sub.3 which may be similar or different, represent each an alkyl radical; the invention also relates to the salts of such compounds, their preparation, intermediates for preparing them and drugs containing them. ##STR1##

  具有以下式（I）的化合物，其中R和R.sub.1，相似或不同，代表氢或卤素原子或基团烷基，烷氧基，氨基，酰胺基，苯基脲基，--N.dbd.CH--N(R.sub.2)R.sub.3，硝基，咪唑基，苯基，SO.sub.3 H或氰基；R.sub.2和R.sub.3可以相同也可以不同，分别代表烷基基团；本发明还涉及这些化合物的盐，它们的制备，用于制备它们的中间体以及含有它们的药物。
• リルゾールおよびＡＭＰＡ受容体アンタゴニストの組み合わせ剤を用いる筋萎縮性側索硬化症の治療
  申请人：アベンテイス・フアルマ・ソシエテ・アノニム

  公开号：JP2002539162A

  公开（公告）日：2002-11-19

  \n (57)【要約】\n本発明は、リルゾールおよび１種もしくは数種のＡＭＰＡ受容体アンタゴニストの組み合わせ剤を用いる筋萎縮性側索硬化症の予防および／もしくは治療、新規組み合わせ剤ならびにそれらを含有する製薬学的組成物に関する。\n

  \(57) [摘要]本发明涉及用利鲁唑和一种或几种AMPA受体拮抗剂的复方制剂、新型复方制剂和含有它们的药物组合物预防和/或治疗肌萎缩侧索硬化症。\n
• DERIVES DE 5H,10H-IMIDAZO[1,2-a]INDENO[1,2-e]PYRAZINE-4-ONE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
  申请人：RHONE-POULENC RORER S.A.

  公开号：EP0662971B1

  公开（公告）日：1998-05-13