10-acetamido-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one | 173155-34-5

• 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: 10-acetamido-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one
• 英文别名: 10-acetamido-10-methyl-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one；10-acetamido-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one；N-(16-methyl-7-oxo-2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10,12,14-hexaen-16-yl)acetamide
• CAS: 173155-34-5
• 化学式: C₁₆H₁₄N₄O₂
• 分子量: 294.313
• InChiKey: FQLZLAZIDUPHBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-acetamido-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one 在 硫酸 、 potassium nitrate 作用下， 反应 1.5h， 以76.5%的产率得到8-nitro-10-acetamido-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one
  参考文献：
  名称：

  8-Methylureido-10-amino-10-methyl-imidazo[1,2- a ]indeno[1,2- e ]pyrazine-4-ones: Highly In vivo Potent and Selective AMPA Receptor Antagonists

  摘要：

  Water soluble 8-methylureido-10-amino-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one 4 represents a novel class of highly potent and selective AMPA receptors antagonists with in vivo activity. The dextrorotatory isomer (+)-4 was found to display the highest affinity with an IC50 of 10 nM. It also exhibited very good anticonvulsant effects after ip, sc and iv administration in mice subjected to electrical convulsions (MES) and ip in audiogenic seizure-e in DBA/2 mice (ED50's less than or equal to 10 mg/kg). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00161-9
• 作为产物：
  描述：

  10-hydroxyimino-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one 在 sodium hydride 、 锌 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 10-acetamido-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one
  参考文献：
  名称：

  Spiro-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one derivatives are mixed AMPA and NMDA glycine-site antagonists active in vivo

  摘要：

  Original spiro-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one derivatives were synthesised and led to the identification of 3e which showed good affinities for both the AMPA and the NMDA glycine-site receptors, and displayed good anticonvulsant effects after i.p. and i.v. administrations in the electroshock-induced convulsion assay in mice. The corresponding dextrorotatory isomer (+)-3e was notably more potent than the levorotatory isomer (-)-3e in in vitro and in vivo assays. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00502-8

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。
• 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
• Spiro-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one derivatives are mixed AMPA and NMDA glycine-site antagonists active in vivo
  作者：Patrick Jimonet、Alain Boireau、Michel Chevé、Dominique Damour、Arielle Genevois-Borella、Assunta Imperato、Jeremy Pratt、John C.R. Randle、Yves Ribeill、Jean-Marie Stutzmann、Serge Mignani

  DOI：10.1016/s0960-894x(99)00502-8

  日期：1999.10

  Original spiro-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one derivatives were synthesised and led to the identification of 3e which showed good affinities for both the AMPA and the NMDA glycine-site receptors, and displayed good anticonvulsant effects after i.p. and i.v. administrations in the electroshock-induced convulsion assay in mice. The corresponding dextrorotatory isomer (+)-3e was notably more potent than the levorotatory isomer (-)-3e in in vitro and in vivo assays. (C) 1999 Elsevier Science Ltd. All rights reserved.
• DERIVES D'IMIDAZO(1,2-A)INDENO(1,2-E)PYRAZIN-4-ONE ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：RHONE-POULENC RORER S.A.

  公开号：EP0752992A1

  公开（公告）日：1997-01-15
• 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