(S)-2-(5-tert-Butyl-2,3-dioxo-3,4-dihydro-2H-pyrazin-1-yl)-butyric acid ethyl ester | 848612-34-0

• 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: (S)-2-(5-tert-Butyl-2,3-dioxo-3,4-dihydro-2H-pyrazin-1-yl)-butyric acid ethyl ester
• CAS: 848612-34-0
• 化学式: C₁₄H₂₂N₂O₄
• 分子量: 282.34
• InChiKey: VCTDXWKNMWUPMG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  81.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(5-tert-Butyl-2,3-dioxo-3,4-dihydro-2H-pyrazin-1-yl)-butyric acid ethyl ester 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 三溴氧磷 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-(2-{5-tert-Butyl-3-[(4-methyl-furazan-3-ylmethyl)-amino]-2-oxo-2H-pyrazin-1-yl}-butyrylamino)-succinic acid 4-tert-butyl ester 1-methyl ester
  参考文献：
  名称：

  Novel pyrazinone mono-amides as potent and reversible caspase-3 inhibitors

  摘要：

  The iterative process for the discovery of a series of pyrazinone mono-amides as potent, selective and reversible non-peptide caspase-3 inhibitors (e.g., M826 and M867) is reported. These compounds display potent anti apoptotic activities in a number of cell based systems in vitro as well as in several animal models in vivo. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.006
• 作为产物：
  描述：

  (S)-2-[(1-Hydroxymethyl-2,2-dimethyl-propylaminooxalyl)-amino]-butyric acid ethyl ester 在 戴斯-马丁氧化剂 、 溶剂黄146 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-2-(5-tert-Butyl-2,3-dioxo-3,4-dihydro-2H-pyrazin-1-yl)-butyric acid ethyl ester
  参考文献：
  名称：

  Novel pyrazinone mono-amides as potent and reversible caspase-3 inhibitors

  摘要：

  The iterative process for the discovery of a series of pyrazinone mono-amides as potent, selective and reversible non-peptide caspase-3 inhibitors (e.g., M826 and M867) is reported. These compounds display potent anti apoptotic activities in a number of cell based systems in vitro as well as in several animal models in vivo. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.006

文献信息

• Solid-phase analogue synthesis of caspase-3 inhibitors via palladium-catalyzed amination of 3-bromopyrazinones
  作者：Elise Isabel、Renee Aspiotis、W. Cameron Black、John Colucci、Réjean Fortin、André Giroux、Erich L. Grimm、Yongxin Han、Christophe Mellon、Donald W. Nicholson、Dita M. Rasper、Johanne Renaud、Sophie Roy、John Tam、Paul Tawa、John P. Vaillancourt、Steven Xanthoudakis、Robert J. Zamboni

  DOI：10.1016/j.bmcl.2006.12.110

  日期：2007.3

  protease that mediates apoptotic cell death. Its inhibition may have an important impact on the treatment of several degenerative diseases. Here we report the synthesis of reversible inhibitors via a solid-support palladium-catalyzed amination of 3-bromopyrazinones and the discovery of a pan-caspase reversible inhibitor.

  Caspase-3是半胱氨酸蛋白酶，介导凋亡的细胞死亡。它的抑制作用可能对几种退行性疾病的治疗产生重要影响。在这里，我们报告通过固相支持钯催化的3-溴吡嗪酮的胺化反应合成可逆抑制剂，以及泛半胱天冬酶可逆抑制剂的发现。