乙基2,5-二氧代-1,3,6,7-四氢吡咯并[1,2-a]咪唑-7alpha-羧酸酯 | 126101-08-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 乙基2,5-二氧代-1,3,6,7-四氢吡咯并[1,2-a]咪唑-7alpha-羧酸酯
• 中文别名: 淀粉状蛋白β-蛋白质(25-35)酰胺
• 英文名称: ethyl 2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazole-7a-carboxylate
• 英文别名: Ethyl 2,5-dioxohexahydro-1H-pyrrolo(1,2-a)imidazole-7a-carboxylate；ethyl 2,5-dioxo-1,3,6,7-tetrahydropyrrolo[1,2-a]imidazole-7a-carboxylate
• CAS: 126101-08-4
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: NMTFYGSVZJZCNA-UHFFFAOYSA-N

物化性质

• 沸点：
  457.6±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙基2,5-二氧代-1,3,6,7-四氢吡咯并[1,2-a]咪唑-7alpha-羧酸酯 在 氨 作用下， 以 甲醇 为溶剂， 以1.7 g (77%)的产率得到2,5-二氧代-1,3,6,7-四氢吡咯并[1,2-a]咪唑-7alpha-甲酰胺
  参考文献：
  名称：

  Psychotropic perhydroazacycloalka [1,2-A] imidazole derivatives

  摘要：

  描述了一种恢复学习能力和治疗记忆困难的咪唑衍生物。该发明的化合物是2,5-二氧代六氢-1H-吡咯[1,2-a]咪唑。

  公开号：

  US05053422A1
• 作为产物：
  描述：

  2-carboxy-4-oxo-2-imidazolidinepropanoic acid 在 盐酸 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 草酰氯 、 N,N-二甲基甲酰胺 、 六甲基二硅氮烷 作用下， 反应 6.67h， 生成 乙基2,5-二氧代-1,3,6,7-四氢吡咯并[1,2-a]咪唑-7alpha-羧酸酯
  参考文献：
  名称：

  Synthesis and pharmacological activity of a series of dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, a novel class of potent cognition enhancers

  摘要：

  A series of dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones were synthesized. These bicylic derivatives contain both the 2-pyrrolidinone and 4-imidazolidinone nuclei, already recognized as important for cognition enhancing activity. In addition, these structures maintain the backbone of piracetam and oxiracetam with the acetamide side chain restricted in a folded conformation. Their ability to reverse scopolamine-induced amnesia was assessed in a one trial, step-through, passive avoidance paradigm. The main features observed are a potent antiamnestic activity after ip administration (minimal effective dose being between 0.3 and 1 mg/kg ip for most compounds), the presence of a bell-shaped dose-response curve and, generally, a reduction of biological activity after po administration. However, the unsubstituted compound (15, dimiracetam) shows no evidence of a bell-shaped dose-response curve and completely retains activity when given orally, being 10-30 times more potent than the reference drug oxiracetam.

  DOI：

  10.1021/jm00078a011

文献信息

• Condensed imidazole derivatives, process and intermediates for their preparation and pharmaceutical compositions containing them.
  申请人：ISF SOCIETA PER AZIONI

  公开号：EP0335483A2

  公开（公告）日：1989-10-04

  Compounds of structure (I) in which, R¹ is hydrogen, C₁₋₄alkyl, CHR⁶CONHR⁷ or CHR⁶COOR⁷ in which R⁶ and R⁷ are each hydrogen or C₁₋₄alkyl; R² is hydrogen, C₁₋₅alkyl or a residue R² of an amino acid R² CH(NH₂)COOH; R³ is hydrogen, C₁₋₄alkyl, CONH₂ or CO₂R⁸ in which R⁸ is hydrogen or C₁₋₄alkyl; and n is 2, 3 or 4, processes for their preparation, intermediates useful in their preparation, pharmaceutical composition containing them and their use in therapy as nootropic agents.

  结构(I)的化合物 其中，R¹ 是氢、C₁₋₄、CHR⁶CONHR⁷ 或 CHR⁶COOR⁷，其中 R⁶ 和 R⁷ 各为氢或 C₁₋₄；R² 是氢、C₁₋₅烷基或氨基酸的残基 R² R² CH(NH₂)COOH；R³ 是氢、C₁₋₄烷基、CONH₂或 CO₂R⁸，其中 R⁸ 是氢或 C₁₋₄烷基；以及 n 是 2、3 或 4。
• Pinza Mario, Farina Carlo, Cerri Alberto, Pfeiffer Ugo, Riccaboni Maria T+, J. Med. Chem, 36 (1993) N 26, S 4214-4220
  作者：Pinza Mario, Farina Carlo, Cerri Alberto, Pfeiffer Ugo, Riccaboni Maria T+

  DOI：——

  日期：——
• US5053422A
  申请人：——

  公开号：US5053422A

  公开（公告）日：1991-10-01
• US5130319A
  申请人：——

  公开号：US5130319A

  公开（公告）日：1992-07-14
• US5200406A
  申请人：——

  公开号：US5200406A

  公开（公告）日：1993-04-06