2-acetamido-N-propan-2-ylprop-2-enamide | 242816-37-1

• 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: 2-acetamido-N-propan-2-ylprop-2-enamide
• CAS: 242816-37-1
• 化学式: C₈H₁₄N₂O₂
• 分子量: 170.211
• InChiKey: NTMSHQZSFRTDDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-acetamido-N-propan-2-ylprop-2-enamide 、 3-phenyl-1,4,2-dioxazol-5-one 在 [(1,2,3,4,5-pentamethylcyclopentadienyl)*Co(CH₃CN)₃](SbF₆)₂ 作用下， 以 2,2,2-三氟乙醇 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以68%的产率得到
  参考文献：
  名称：

  钴 (III) 催化脱氢丙氨酸的 CH 酰胺化，用于硫链丝菌肽的位点选择性结构多样化。

  摘要：

  硫链丝菌素是一种针对多种革兰氏阳性菌的有效抗生素，但其医疗应用因其水溶性差而受到限制。本工作首次将脱氢丙氨酸(Dha)残基的C(sp2)-H酰胺化应用于硫链丝菌肽的位点选择性修饰，制备了多种衍生物。与所有现有的硫链丝菌肽修饰方法不同，Dha 残基的烯烃骨架得以保留，并且对 Z-立体异构体具有完全选择性。此外，通过 CH 酰胺化引入醛基，使肟连接能够安装更广泛的功能。硫链丝菌素衍生物通常保持抗菌活性，重要的是，其中八种衍生物的水溶性得到改善（高达 28 倍），从而解决了这种抗生素的一个关键缺点。CoIII 催化的 C(sp2 )-H Dha 酰胺化的特殊官能团相容性和位点选择性表明该方法可以推广到含有 Dha 残基的其他天然产物和生物聚合物。

  DOI：

  10.1002/anie.201911886
• 作为产物：
  描述：

  2-乙酰氨基丙烯酸 、 异丙胺 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 2-acetamido-N-propan-2-ylprop-2-enamide
  参考文献：
  名称：

  Evaluation of rat kidney aldose reductase inhibitory activity of some N-acetyl dehydroalanine derivatives

  摘要：

  Aldose reductase (AR) is an enzyme that catalyzes the conversion of glucose to sorbitol, which is in turn converted to fructose by sorbitol dehydrogenase. Increased AR activity has been implicated in the pathogenesis of diabetic complications such as neuropathy, nephropathy, retinopathy, and cataract. Inhibitors of AR thus seem to have the potential to prevent or treat diabetic complications. At present, however, side effects and/or insufficient pharmacokinetic profiles have made most of the drug candidates undesirable. In this study, the synthesis (l-o) and ARI activity of 15 N-acetyl dehydroalanine derivatives (a-o) are described. The synthesized compounds mainly contained aliphatic and aromatic side chains. The insertion of ethyl and chloro propyl side chains were shown to be more effective than the rest of the compounds. Between the synthesized compounds N-ethyl (b) and N-propylchloride (h) derivatives showed the best ARI activities.

  DOI：

  10.1007/s00044-010-9337-y

文献信息

• Cobalt(III)‐Catalyzed C−H Amidation of Dehydroalanine for the Site‐Selective Structural Diversification of Thiostrepton
  作者：Ryan J. Scamp、Edward deRamon、Eric K. Paulson、Scott J. Miller、Jonathan A. Ellman

  DOI：10.1002/anie.201911886

  日期：2020.1.7

  Thiostrepton is a potent antibiotic against a broad range of Gram-positive bacteria, but its medical applications have been limited by its poor aqueous solubility. In this work, the first C(sp2 )-H amidation of dehydroalanine (Dha) residues was applied to the site selective modification of thiostrepton to prepare a variety of derivatives. Unlike all prior methods for the modification of thiostrepton

  硫链丝菌素是一种针对多种革兰氏阳性菌的有效抗生素，但其医疗应用因其水溶性差而受到限制。本工作首次将脱氢丙氨酸(Dha)残基的C(sp2)-H酰胺化应用于硫链丝菌肽的位点选择性修饰，制备了多种衍生物。与所有现有的硫链丝菌肽修饰方法不同，Dha 残基的烯烃骨架得以保留，并且对 Z-立体异构体具有完全选择性。此外，通过 CH 酰胺化引入醛基，使肟连接能够安装更广泛的功能。硫链丝菌素衍生物通常保持抗菌活性，重要的是，其中八种衍生物的水溶性得到改善（高达 28 倍），从而解决了这种抗生素的一个关键缺点。CoIII 催化的 C(sp2 )-H Dha 酰胺化的特殊官能团相容性和位点选择性表明该方法可以推广到含有 Dha 残基的其他天然产物和生物聚合物。
• Evaluation of rat kidney aldose reductase inhibitory activity of some N-acetyl dehydroalanine derivatives
  作者：Net Das-Evcimen、Mutlu Sarikaya、Gokce Gurkok、Sibel Suzen

  DOI：10.1007/s00044-010-9337-y

  日期：2011.5

  Aldose reductase (AR) is an enzyme that catalyzes the conversion of glucose to sorbitol, which is in turn converted to fructose by sorbitol dehydrogenase. Increased AR activity has been implicated in the pathogenesis of diabetic complications such as neuropathy, nephropathy, retinopathy, and cataract. Inhibitors of AR thus seem to have the potential to prevent or treat diabetic complications. At present, however, side effects and/or insufficient pharmacokinetic profiles have made most of the drug candidates undesirable. In this study, the synthesis (l-o) and ARI activity of 15 N-acetyl dehydroalanine derivatives (a-o) are described. The synthesized compounds mainly contained aliphatic and aromatic side chains. The insertion of ethyl and chloro propyl side chains were shown to be more effective than the rest of the compounds. Between the synthesized compounds N-ethyl (b) and N-propylchloride (h) derivatives showed the best ARI activities.