(2S)-2-((叔丁氧基羰基)氨基)-3-(2-氧代吡咯烷-3-基)丙酸甲酯 | 1350624-45-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: (2S)-2-((叔丁氧基羰基)氨基)-3-(2-氧代吡咯烷-3-基)丙酸甲酯
• 英文名称: (2S)-methyl 2-(tert-butoxycarbonylamino)-3-(2-oxopyrrolidin-3-yl) propanoate
• 英文别名: Methyl (2S)-2-((tert-butoxycarbonyl)amino)-3-(2-oxopyrrolidin-3-yl)propanoate；methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(2-oxopyrrolidin-3-yl)propanoate
• CAS: 1350624-45-1
• 化学式: C₁₃H₂₂N₂O₅
• 分子量: 286.328
• InChiKey: HTQMBOWAEPNWLI-GKAPJAKFSA-N

物化性质

• 沸点：
  471.5±20.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-((叔丁氧基羰基)氨基)-3-(2-氧代吡咯烷-3-基)丙酸甲酯 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-((S)-2-((((苄氧基)羰基)氨基)-4-甲基戊酰氨基)-3-(2-氧代
  参考文献：
  名称：

  Potent inhibition of norovirus 3CL protease by peptidyl α-ketoamides and α-ketoheterocycles

  摘要：

  A series of structurally-diverse alpha-ketoamides and alpha-ketoheterocycles was synthesized and subsequently investigated for inhibitory activity against norovirus 3CL protease in vitro, as well as anti-norovirus activity in a cell-based replicon system. The synthesized compounds were found to inhibit norovirus 3CL protease in vitro and to also exhibit potent anti-norovirus activity in a cell-based replicon system. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.055
• 作为产物：
  描述：

  (4S)-dimethyl 2-(2-aminoethyl)-4-((tert-butoxycarbonyl)amino)pentanedioate 、 三乙胺 、 水 在 二氯甲烷 、 Sodium sulfate-III 、 silica gel 、 heptanes EtOAc 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以to afford (2S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2-oxopyrrolidin-3-yl)propanoate (5.5 g, 60% yield over two steps) as a light brown oil的产率得到(2S)-2-((叔丁氧基羰基)氨基)-3-(2-氧代吡咯烷-3-基)丙酸甲酯
  参考文献：
  名称：

  TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS

  摘要：

  本文提供了三肽环氧酮蛋白酶抑制剂及其制备方法、相关药物组合物和使用方法。例如，本文提供了式（X）的化合物及其药物可接受的盐和组合物。本文提供的化合物和组合物可以用于治疗包括炎症和神经退行性疾病在内的疾病。

  公开号：

  US20140336106A1

文献信息

• [EN] TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE TRIPEPTIDE ÉPOXY CÉTONE PROTÉASE
  申请人：ONYX THERAPEUTICS INC

  公开号：WO2014152134A1

  公开（公告）日：2014-09-25

  Provided herein are tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of diseases including inflammation and neurodegenerative disease.

  本文提供了三肽环氧酮蛋白酶抑制剂，它们的制备方法，相关的药物组合物，以及使用它们的方法。例如，本文提供了式（X）的化合物：以及包括它们的药物可接受的盐和组合物。本文提供的化合物和组合物可以用于治疗炎症和神经退行性疾病等疾病。
• TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS
  申请人：Onyx Therapeutics, Inc.

  公开号：US20140336106A1

  公开（公告）日：2014-11-13

  Provided herein are tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of diseases including inflammation and neurodegenerative disease.

  本文提供了三肽环氧酮蛋白酶抑制剂及其制备方法、相关药物组合物和使用方法。例如，本文提供了式（X）的化合物及其药物可接受的盐和组合物。本文提供的化合物和组合物可以用于治疗包括炎症和神经退行性疾病在内的疾病。
• Design, synthesis, and evaluation of inhibitors of Norwalk virus 3C protease
  作者：Kok-Chuan Tiew、Guijia He、Sridhar Aravapalli、Sivakoteswara Rao Mandadapu、Mallikarjuna Reddy Gunnam、Kevin R. Alliston、Gerald H. Lushington、Yunjeong Kim、Kyeong-Ok Chang、William C. Groutas

  DOI：10.1016/j.bmcl.2011.07.016

  日期：2011.9

  The first series of peptidyl aldehyde inhibitors that incorporate in their structure a glutamine surrogate has been designed and synthesized based on the known substrate specificity of Norwalk virus 3C protease. The inhibitory activity of the compounds with the protease and with a norovirus cell-based replicon system was investigated. Members of this class of compounds exhibited noteworthy activity both in vitro and in a cell-based replicon system. (C) 2011 Elsevier Ltd. All rights reserved.
• BROAD-SPECTRUM ANTIVIRALS AGAINST 3C OR 3C-LIKE PROTEASES OF PICORNAVIRUS-LIKE SUPERCLUSTER: PICORNAVIRUSES, CALICIVIRUSES AND CORONAVIRUSES
  申请人：Kansas State University Research Foundation

  公开号：US20140243341A1

  公开（公告）日：2014-08-28

  Antiviral protease inhibitors, including peptidyl aldehydes, peptidyl α-ketoamides, peptidyl bisulfite salts, and peptidyl heterocycles, are disclosed, along with related antiviral compounds, and methods of using the same to treat or prevent viral infection and disease. The compounds possess broad-spectrum activity against viruses that belong to the picornavirus-like supercluster, which include important human and animal pathogens including noroviruses, enteroviruses, poliovirus, foot-and-mouth disease virus, hepatitis A virus, human rhinovirus (cause of common cold), human coronavirus (another cause of common cold), transmissible gastroenteritis virus, murine hepatitis virus, feline infectious peritonitis virus, and severe acute respiratory syndrome coronavirus.
• US9434761B2
  申请人：——

  公开号：US9434761B2

  公开（公告）日：2016-09-06