Ethyl 1-(6-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate | 156484-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: Ethyl 1-(6-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate
• 英文别名: ethyl 1-(5-chloro-3-oxo-1,2-dihydroinden-2-yl)imidazole-2-carboxylate
• CAS: 156484-52-5
• 化学式: C₁₅H₁₃ClN₂O₃
• 分子量: 304.733
• InChiKey: BYLPGDBLFRFLIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 1-(6-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate 在 盐酸 、 氨 作用下， 以 甲醇 为溶剂， 生成 7-chloro-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：

  咪唑-2-甲酸乙酯 、 2-bromo-6-chloro-1-indanone 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 1-(6-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate
  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

• 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##

  化合物的式子为（I），其中R和R.sub.1，相同或不同，表示氢原子、卤素或基团烷基、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，可以相同或不同，表示各自的烷基基团；本发明还涉及这种化合物的盐、其制备、制备它们的中间体和含有它们的药物。
• US5677306A
  申请人：——

  公开号：US5677306A

  公开（公告）日：1997-10-14
• 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.