2-carboxy-4-oxo-2-imidazolidinepropanoic acid | 126101-23-3

• 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
• 英文名称: 2-carboxy-4-oxo-2-imidazolidinepropanoic acid
• 英文别名: 2-carboxy-4-oxo-2-imidazolidine-propanoic acid；2-(2-carboxyethyl)-4-oxoimidazolidine-2-carboxylic acid
• CAS: 126101-23-3
• 化学式: C₇H₁₀N₂O₅
• 分子量: 202.167
• InChiKey: OCJZYNANYYCWKX-UHFFFAOYSA-N

物化性质

• 沸点：
  627.8±55.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-carboxy-4-oxo-2-imidazolidinepropanoic acid 在 盐酸 、 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 6.17h， 生成 2,5-Dioxo-tetrahydro-pyrrolo[1,2-a]imidazole-7a-carbonyl chloride
  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
• 作为产物：
  描述：

  alpha-酮戊二酸 、 甘氨酰胺盐酸盐 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以43%的产率得到2-carboxy-4-oxo-2-imidazolidinepropanoic acid
  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：EP0335483A3

  公开（公告）日：1991-12-18

  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.

  结构式（I）的化合物中，其中R¹为氢，C₁₋₄烷基，CHR⁶CONHR⁷或CHR⁶COOR⁷，其中R⁶和R⁷均为氢或C₁₋₄烷基；R²为氢，C₁₋₅烷基或氨基酸R² CH（NH₂）COOH的残基R²；R³为氢，C₁₋₄烷基，CONH₂或CO₂R⁸，其中R⁸为氢或C₁₋₄烷基；n为2、3或4，其制备方法，用于其制备的中间体，包含它们的制药组合物以及它们作为神经营养剂在治疗中的用途。
• Psychotropic perhydroazacycloalka [1,2-A] imidazole derivatives
  申请人：I.S.F. Societa per Azioni

  公开号：US05053422A1

  公开（公告）日：1991-10-01

  Imidazole derivatives are described which are useful in restoring learning and treating memory difficulties. A compound of the invention is 2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazole.

  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。
• Pharmaceutically useful 2,5-dioxo-1H-octahydroimidazo[1,2-A]azepines
  申请人：I.S.F. Societa per Azioni

  公开号：US05200406A1

  公开（公告）日：1993-04-06

  Imidazole derivatives are described which are useful in restoring learning and treating memory difficulties. A compound of the invention is 2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazole.

  本文描述了一种有益于恢复学习和治疗记忆障碍的咪唑衍生物。该发明的化合物是2,5-二氧代六氢-1H-吡咯并[1,2-a]咪唑。
• Pharmacologically active 2,5-dioxo-octahydro-imidazo [1,2-a]pyridines
  申请人：I.S.F. Societa per Azioni

  公开号：US05130319A1

  公开（公告）日：1992-07-14

  Imidazole derivatives are described which are useful in restoring learning and treating memory difficulties. A compound of the invention is 2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazole.

  本发明描述了一种有用于恢复学习和治疗记忆障碍的咪唑衍生物。本发明的一种化合物是2,5-二氧代六氢-1H-吡咯并[1,2-a]咪唑。
• 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：——