ethyl 2-[[(3S)-2-hydroxy-3-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-4-(2-oxopyrrolidin-3-yl)butanoyl]amino]acetate | 1385183-73-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: ethyl 2-[[(3S)-2-hydroxy-3-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-4-(2-oxopyrrolidin-3-yl)butanoyl]amino]acetate
• CAS: 1385183-73-2
• 化学式: C₂₆H₃₈N₄O₈
• 分子量: 534.61
• InChiKey: IQTDQNBMQILIHN-KBNVZVJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-[[(3S)-2-hydroxy-3-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-4-(2-oxopyrrolidin-3-yl)butanoyl]amino]acetate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-[[(3S)-3-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-2-oxo-4-(2-oxopyrrolidin-3-yl)butanoyl]amino]acetate
  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：

  (2S)-2-((S)-2-((((苄氧基)羰基)氨基)-4-甲基戊酰氨基)-3-(2-氧代 在 甲醇 、 锂硼氢 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 ethyl 2-[[(3S)-2-hydroxy-3-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-4-(2-oxopyrrolidin-3-yl)butanoyl]amino]acetate
  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

文献信息

• 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.
• US9474759B2
  申请人：——

  公开号：US9474759B2

  公开（公告）日：2016-10-25
• Potent inhibition of norovirus 3CL protease by peptidyl α-ketoamides and α-ketoheterocycles
  作者：Sivakoteswara Rao Mandadapu、Pathum M. Weerawarna、Mallikarjuna Reddy Gunnam、Kevin R. Alliston、Gerald H. Lushington、Yunjeong Kim、Kyeong-Ok Chang、William C. Groutas

  DOI：10.1016/j.bmcl.2012.05.055

  日期：2012.7

  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.