(S)-alpha-氨基-2,3,4,5,6,7-六氢-2,4-二氧代-1H-环戊并嘧啶-1-丙酸 | 389888-02-2

• 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: (S)-alpha-氨基-2,3,4,5,6,7-六氢-2,4-二氧代-1H-环戊并嘧啶-1-丙酸
• 英文名称: (S)-CPW 399
• 英文别名: (S)-2-Amino-3-(1,3,5,7-pentahydro-2,4-dioxo-cyclopenta[E]pyrimidin-1-YL) proionic acid；(2S)-2-amino-3-(2,4-dioxo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-1-yl)propanoic acid
• CAS: 389888-02-2
• 化学式: C₁₀H₁₃N₃O₄
• 分子量: 239.231
• InChiKey: VSGUEKZRMJVQOH-LURJTMIESA-N

物化性质

• 熔点：
  >163°C (dec.)
• 溶解度：
  可溶于酸水溶液（轻微、加热、超声处理）、DMSO（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2,3,5,6,7-六氢-2-硫氧代-4H-环戊并嘧啶-4-酮 在 sodium hydride 、 氯乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (S)-alpha-氨基-2,3,4,5,6,7-六氢-2,4-二氧代-1H-环戊并嘧啶-1-丙酸
  参考文献：
  名称：

  Characterization of the 1H-Cyclopentapyrimidine-2,4(1H,3H)-dione Derivative (S)-CPW399 as a Novel, Potent, and Subtype-Selective AMPA Receptor Full Agonist with Partial Desensitization Properties

  摘要：

  (S)-CPW399 (2b) is a novel, potent, and subtype-selective AMPA receptor full agonist that, unlike (S)-willardiine and related compounds, in mouse cerebellar granule cells, stimulated an increase in [Ca2+](i), and induced neuronal cell death in a time- and concentration-dependent manner. Compound 2b appears to be a weakly desensitizing, full agonist at AMPA receptors and therefore represents a new pharmacological tool to investigate the role of AMPA receptors in excitotoxicity and their molecular mechanisms of desensitization.

  DOI：

  10.1021/jm015552m

文献信息

• COMPOSITIONS AND METHODS FOR TREATING METABOLIC DISORDERS
  申请人：VeroScience LLC

  公开号：EP3311842A1

  公开（公告）日：2018-04-25

  The application discloses methods and compositions for regulating neuronal activities in the brain that are useful, for example, for treating metabolic disorders.

  该申请公开了调节大脑神经元活动的方法和组合物，这些方法和组合物可用于治疗代谢紊乱等疾病。
• Compositions and Methods for Treating Metabolic Disorders
  申请人：VeroScience LLC

  公开号：US20150011554A1

  公开（公告）日：2015-01-08

  The application discloses methods and compositions for regulating neuronal activities in the brain that are useful, for example, for treating metabolic disorders.
• Characterization of the 1<i>H</i>-Cyclopentapyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione Derivative (S)-CPW399 as a Novel, Potent, and Subtype-Selective AMPA Receptor Full Agonist with Partial Desensitization Properties
  作者：Giuseppe Campiani、Elena Morelli、Vito Nacci、Caterina Fattorusso、Anna Ramunno、Ettore Novellino、Jeremy Greenwood、Tommy Liljefors、Roger Griffiths、Colin Sinclair、Helen Reavy、Anders S. Kristensen、Darryl S. Pickering、Arne Schousboe、Alfredo Cagnotto、Elena Fumagalli、Tiziana Mennini

  DOI：10.1021/jm015552m

  日期：2001.12.1

  (S)-CPW399 (2b) is a novel, potent, and subtype-selective AMPA receptor full agonist that, unlike (S)-willardiine and related compounds, in mouse cerebellar granule cells, stimulated an increase in [Ca2+](i), and induced neuronal cell death in a time- and concentration-dependent manner. Compound 2b appears to be a weakly desensitizing, full agonist at AMPA receptors and therefore represents a new pharmacological tool to investigate the role of AMPA receptors in excitotoxicity and their molecular mechanisms of desensitization.