(3S)-3-氨基-3-吡咯烷羧酸 | 113473-30-6

• 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: (3S)-3-氨基-3-吡咯烷羧酸
• 英文名称: (S)-(-)-cucurbitine
• 英文别名: (3S)-3-aminopyrrolidin-1-ium-3-carboxylate
• CAS: 113473-30-6
• 化学式: C₅H₁₀N₂O₂
• mdl: MFCD09971714
• 分子量: 130.147
• InChiKey: DWAKXSZUASEUHH-YFKPBYRVSA-N

物化性质

• 熔点：
  230 °C
• 沸点：
  279.0±40.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (3S)-3-氨基-3-吡咯烷羧酸 在 2,4,6-三甲基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 sodium cyanoborohydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.75h， 生成 (E)-3-{4-[((S)-3-amino-1-methylpyrrolidine-3-carbonyl)-amino]phenyl}acrylic acid ethyl ester
  参考文献：
  名称：

  Discovery of the First Thumb Pocket 1 NS5B Polymerase Inhibitor (BILB 1941) with Demonstrated Antiviral Activity in Patients Chronically Infected with Genotype 1 Hepatitis C Virus (HCV)

  摘要：

  Combinations of direct acting antivirals (DAAs) that have the potential to suppress emergence of resistant virus and that can be used in interferon-sparing regimens represent a preferred option for the treatment of chronic HCV infection. We have discovered allosteric (thumb pocket 1) non-nucleoside inhibitors of HCV NS5B polymerase that inhibit replication in replicon systems. Herein, we report the late-stage optimization of indole-based inhibitors, which began with the identification of a metabolic liability common to many previously reported inhibitors in this series. By use of parallel synthesis techniques, a sparse matrix of inhibitors was generated that provided a collection of inhibitors satisfying potency criteria and displaying improved in vitro ADME profiles. "Cassette" screening for oral absorption in rat provided a short list of potential development candidates. Further evaluation led to the discovery of the first thumb pocket 1 NS5B inhibitor (BILB 1941) that demonstrated antiviral activity in patients chronically infected with genotype 1 HCV.

  DOI：

  10.1021/jm3006788
• 作为产物：
  描述：

  (-)-N-benzyl-3-aminopyrrolidine-3-carboxylic acid 以91%的产率得到
  参考文献：
  名称：

  MORIMOTO, YOSHIHISA;ACHIWA, KAZUO, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3845-3849

  摘要：

  DOI：

文献信息

• Asymmetric synthesis of S-(−)-cucurbitine
  作者：Robert M. Williams、Glenn J. Fegley

  DOI：10.1016/s0040-4039(00)61768-9

  日期：1992.11

  The asymmetric synthesis of (S)-(−)-cucurbitine in greater than 98 % ee is described. The key step of the synthesis involves 1,3-dipolar cycloaddition of azomethine ylide (1)1 to α,β-dehydrolactone (3) to give pyrrolidine (6) as a single diastereomer.

  描述了大于98％ee的（S）-（-）-葫芦素的不对称合成。合成的关键步骤涉及将甲亚胺叶立德（1）1与α，β-脱氢内酯（3）进行1,3-偶极环加成反应，得到吡咯烷（6），为单一非对映异构体。
• MORIMOTO, YOSHIHISA;ACHIWA, KAZUO, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3845-3849
  作者：MORIMOTO, YOSHIHISA、ACHIWA, KAZUO

  DOI：——

  日期：——
• Discovery of the First Thumb Pocket 1 NS5B Polymerase Inhibitor (BILB 1941) with Demonstrated Antiviral Activity in Patients Chronically Infected with Genotype 1 Hepatitis C Virus (HCV)
  作者：Pierre L. Beaulieu、Michael Bös、Michael G. Cordingley、Catherine Chabot、Gulrez Fazal、Michel Garneau、James R. Gillard、Eric Jolicoeur、Steven LaPlante、Ginette McKercher、Martin Poirier、Marc-André Poupart、Youla S. Tsantrizos、Jianmin Duan、George Kukolj

  DOI：10.1021/jm3006788

  日期：2012.9.13

  Combinations of direct acting antivirals (DAAs) that have the potential to suppress emergence of resistant virus and that can be used in interferon-sparing regimens represent a preferred option for the treatment of chronic HCV infection. We have discovered allosteric (thumb pocket 1) non-nucleoside inhibitors of HCV NS5B polymerase that inhibit replication in replicon systems. Herein, we report the late-stage optimization of indole-based inhibitors, which began with the identification of a metabolic liability common to many previously reported inhibitors in this series. By use of parallel synthesis techniques, a sparse matrix of inhibitors was generated that provided a collection of inhibitors satisfying potency criteria and displaying improved in vitro ADME profiles. "Cassette" screening for oral absorption in rat provided a short list of potential development candidates. Further evaluation led to the discovery of the first thumb pocket 1 NS5B inhibitor (BILB 1941) that demonstrated antiviral activity in patients chronically infected with genotype 1 HCV.