fasoracetam | 110958-23-1

• 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: fasoracetam
• 英文别名: (5S)-5-[(piperidin-1-yl)carbonyl]pyrrolidin-2-one；(2S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one；(5S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one
• CAS: 110958-23-1
• 化学式: C₁₀H₁₆N₂O₂
• 分子量: 196.249
• InChiKey: GOWRRBABHQUJMX-QMMMGPOBSA-N

物化性质

• 沸点：
  456.8±38.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  fasoracetam 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%的产率得到1-[(2S)-吡咯烷甲基]哌啶
  参考文献：
  名称：

  Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

  摘要：

  Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N- methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00579-7
• 作为产物：
  描述：

  哌啶盐酸盐 、 L-焦谷氨酸甲酯 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以52%的产率得到fasoracetam
  参考文献：
  名称：

  DIBAL–H–H 2 NR和DIBAL–H–HNR 1 R 2 ·HCl配合物，可有效地将内酯和酯转化为酰胺

  摘要：

  内酯或酯与DIBAL–H–H 2 NR或DIBAL–H–HNR 1 R 2 ·HCl配合物生成的有机铝的反应提供了制备酰胺的有效方法。定义了制备优异产率的仲酰胺和叔酰胺（包括Weinreb酰胺）的条件。

  DOI：

  10.1016/s0040-4039(01)01933-5

文献信息

• Insights into the Reaction Mechanism of the Prolyl–Acyl Carrier Protein Oxidase Involved in Anatoxin-a and Homoanatoxin-a Biosynthesis
  作者：Stéphane Mann、Bérangère Lombard、Damarys Loew、Annick Méjean、Olivier Ploux

  DOI：10.1021/bi200892a

  日期：2011.8.23

  for the biosynthesis of these toxins as well as the in-vitro reconstitution of the first steps of this biosynthesis. We now report experimental evidence supporting the proposed reaction mechanism of AnaB, a flavoprotein homologous to acyl-CoA dehydrogenase. AnaB catalyzes the two-electron oxidation of prolyl-AnaD, which is proline linked to the acyl carrier protein holo-AnaD, to dehydroprolyl-AnaD

  Anatoxin-a和homoanatoxin-a是两种有效的蓝细菌神经毒素。我们最近报道了负责这些毒素的生物合成以及该生物合成第一步的体外重建的基因簇的鉴定。我们现在报告支持AnaB（一种与酰基辅酶A脱氢酶同源的黄素蛋白）的拟议反应机制的实验证据。AnaB催化脯氨酸与酰基载体蛋白holo-AnaD连接的脯氨酸的双电子氧化，以氧气为第二种底物，将脯氨酰-AnaD氧化为脱氢脯氨酰-AnaD。因此，AnaB是一种氧化酶。通过使用液相色谱与串联质谱联用（LC-MS / MS），我们已经鉴定并表征了AnaB产品脱氢脯氨酰-AnaD。我们估计了1 min –1的表观催化常数。用于AnaB催化。我们合成了几种氘标记的脯氨酸，并通过酶法将其转化为相应的脯氨酰-AnaD。这些氘标记的脯氨酰AnaD在AnaB存在下被氧化，并通过LC-MS / MS测定剩余底物中和产物中的氘标记。数据支持了一种反应机理，该机
• JPS63146857A
  申请人：——

  公开号：JPS63146857A

  公开（公告）日：1988-06-18
• METHOD FOR TREATING APATHY SYNDROME
  申请人：Cha Albert

  公开号：US20100048634A1

  公开（公告）日：2010-02-25

  The present invention provides a method of treating apathy syndrome in a human subject. The human subject is first evaluated to determine whether one or more behavioral characteristics of apathy are observed. If such characteristics are observed, the subject is treated with a 2-oxopyrrolidine compound, such as nefiracetam, piracetam, aniracetam, pramiracetam, nebracetam, fasoracetam, levetiracetam, or oxiracetam, in an amount effective to produce an improvement in such apathy characteristics. The present invention is useful in treating apathy in a subject suffering from conditions associated with or characterized by frontal-subcortical dysfunction. The present invention is also useful in treating apathy in a subject suffering from a stroke, Alzheimer's disease, Parkinson's disease, traumatic brain injury, depression, schizophrenia, chronic hepatitis C infection, or HIV infection.
• CAUSAL THERAPY OF DISEASES OR CONDITIONS ASSOCIATED WITH CNS OR PNS DEMYELINATION
  申请人：Pickering Mark

  公开号：US20120269762A1

  公开（公告）日：2012-10-25

  The invention broadly relates to the use of the Active in the causal treatment of a disease caused by axonal demyelination, in which the Active maintains the integrity of myelination (for example by promoting remyelination, and/or preventing demyelination, of the axonal sheaths). The invention is particularly directed to the causal treatment of CNS demyelination diseases, for example MS, especially primary progressive MS and/or relapse remitting MS, and PNS demyelination diseases, for example Charcot-Marie-Tooth Disease. The Active of the invention may be suitably administered when a patient is in relapse (i.e. upon relapse), and be continued while the patient is in relapse, with a view to attenuating the severity of the relapse, and/or accelerating disease remission. Alternatively, the Active may be administered continuously with a view to prolonging the remission period, and/or attenuating the severity of the relapse, and/or preventing relapse. The invention also relates to the use of the Active as a treatment for symptoms of demyelination disease, especially MS, selected from vision deficits, motor control deficits, and sensation deficits.
• US5102882A
  申请人：——

  公开号：US5102882A

  公开（公告）日：1992-04-07