methyl (S)-1-(2-methoxy-1-methyl-2-oxoethyl)-(S)-aziridine-2-carboxylate | 84674-12-4

• 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: methyl (S)-1-(2-methoxy-1-methyl-2-oxoethyl)-(S)-aziridine-2-carboxylate
• 英文别名: methyl (2S)-1-[(2S)-1-methoxy-1-oxopropan-2-yl]aziridine-2-carboxylate
• CAS: 84674-12-4
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: FXMLKVDNSKCHDD-NCYRLESRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.59
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.61
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2,3-二溴丙酸甲酯 、 3-酞酰亚胺基丙酸甲酯 生成 methyl (S)-1-(2-methoxy-1-methyl-2-oxoethyl)-(S)-aziridine-2-carboxylate
  参考文献：
  名称：

  EREMEEV, A. V.;POLYAK, F. D.;VOSEKALNA, I. A.;CHERVIN, I. I.;NASIBOV, SH.+, XIMIYA GETEROTSIKL. SOEDIN., 1984, N 10, 1343-1348

  摘要：

  DOI：

文献信息

• Small ring constrained peptidomimetics. Synthesis of aziridine parallel β-sheet mimetics
  作者：Silvia N. Filigheddu、Maurizio Taddei

  DOI：10.1016/s0040-4039(98)00632-7

  日期：1998.5

  a series of novel amino acids and peptides containing an aziridine ring is described. Their preparation is based on the Gabriel-Cromwell reaction of amino acids or peptides with different 2-bromo acrylates and acrylamides. These products are constituted by a turned scaffold (the aziridine) where two parallel peptidic strands can be grown to produce a β-sheet mimetic.

  描述了一系列含有氮丙啶环的新型氨基酸和肽的合成。它们的制备基于氨基酸或肽与不同的2-溴丙烯酸酯和丙烯酰胺的Gabriel-Cromwell反应。这些产物由翻转的支架（氮丙啶）构成，其中两条平行的肽链可以生长以产生β-折叠模拟物。
• Screening of electrophilic compounds yields an aziridinyl peptide as new active-site directed SARS-CoV main protease inhibitor
  作者：Erika Martina、Nikolaus Stiefl、Björn Degel、Franziska Schulz、Alexander Breuning、Markus Schiller、Radim Vicik、Knut Baumann、John Ziebuhr、Tanja Schirmeister

  DOI：10.1016/j.bmcl.2005.09.012

  日期：2005.12

  The coronavirus main protease, M-pro, is considered a major target for drugs suitable to combat coronavirus infections including the severe acute respiratory syndrome (SARS). In this study, comprehensive HPLC- and FRET-substrate-based screenings of various electrophilic compounds were performed to identify potential M-pro inhibitors. The data revealec that the coronaviral main protease is inhibited by aziridine- and oxirane-2-carboxylates. Among the trans-configured aziridine-2.3-dicarboxylates the Gly-Gly-containing peptide 2c was found to be the most potent inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.