N-benzyl-1-H-L-aziridine-2-carboxamide | 790692-11-4

• 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: N-benzyl-1-H-L-aziridine-2-carboxamide
• 英文别名: (S)-N-benzyl aziridine-2-carboxamide；(2S)-N-benzylaziridine-2-carboxamide
• CAS: 790692-11-4
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: CCPIHWLRHUYGOW-VIFPVBQESA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  409.4±44.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-H-L-aziridine-2-carboxamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 72.3h， 生成
  参考文献：
  名称：

  硫醇与含氮丙啶-2-羧酸肽的位点选择性偶联

  摘要：

  描述了含氮丙啶-2-羧酸的肽与硫醇在溶液和固体支持物上的合成和会聚位点选择性偶联。FmocAzyOH 在这种能力下的合成和使用证明了 Azy 部分在多步 Fmoc 固相肽合成 (SPPS) 中的有效掺入和耐受性，以及通过高度区域选择性碱基进行溶液和珠上连接的能力。促进氮丙啶开环过程。

  DOI：

  10.1021/ja046793x
• 作为产物：
  描述：

  N-Benzyl-L-serinamide 在 DTPP 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以1.83 g的产率得到N-benzyl-1-H-L-aziridine-2-carboxamide
  参考文献：
  名称：

  Lacosamide Isothiocyanate-Based Agents: Novel Agents To Target and Identify Lacosamide Receptors

  摘要：

  (R)-Lacosamide ((R)-2, (R)-N-benzyl 2-acetamido-3-methoxypropionamide) has recently gained regulatory approval for the treatment of partial-onset seizures in adults. Whole animal pharmacological studies have documented that (R)-2 function is unique: A robust strategy is advanced for the discovery of interacting proteins associated with function and toxicity of (R)-2 through the use of (R)-2 analogues, 3, which contain "affinity bait (AB)" and "chemical reporter (CR)" functional groups. In 3, covalent modification of the interacting proteins proceeds at the AB moiety, and detection or isolation of the selectively captured protein occurs through the bioorthogonal CR group upon reaction with all appropriate probe. We report the synthesis, pharmacological evaluation, and interrogation of the mouse soluble brain proteome using 3 where the AB group is an isothiocyanate moiety. One compound, (R)-N-(4-isothiocyanato)benzyl 2-acetamido-3-(prop-2-ynyloxy)propionamide ((R)-9), exhibited excellent Seizure protection in mice, and like (R)-2, anticonvulsant activity principally resided in the (R)-stereoisomer. Several proteins were preferentially labeled by (R)-9 compared with (S)-9, including collapsin response mediator protein 2.

  DOI：

  10.1021/jm9012054

文献信息

• Ring-Opening of Aziridine-2-Carboxamides with Carbohydrate C1-<i>O</i>-Nucleophiles. Stereoselective Preparation of α- and β-<i>O</i>-Glycosyl Serine Conjugates
  作者：Daniel A. Ryan、David Y. Gin

  DOI：10.1021/ja804589j

  日期：2008.11.19

  The stereoselective formation of the alpha-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the alpha- or beta-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the B-GlcNAc-Ser and alpha-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation.