(S)-N-(allyloxycarbonyl)phenylalanine thioamide | 1607794-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-(allyloxycarbonyl)phenylalanine thioamide
• CAS: 1607794-56-8
• 化学式: C₁₃H₁₆N₂O₂S
• 分子量: 264.348
• InChiKey: SZAWAKINYBIJFW-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.35
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(allyloxycarbonyl)phenylalanine thioamide 在 2,6-二甲基吡啶 、 potassium hydrogencarbonate 、 三氟乙酸酐 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 18.0h， 生成 2-<(S)-1-allyloxycarbonylamino-2-phenyl-ethyl>-4-carboxythiazole
  参考文献：
  名称：

  Dissecting the Structure of Thiopeptides: Assessment of Thiazoline and Tail Moieties of Baringolin and Antibacterial Activity Optimization

  摘要：

  Several analogues of baringolin (1) were prepared to evaluate the role of its characteristic thiazoline ring and pentapeptidic tail with the aim of defining structure activity relationships for these moieties. The thiazoline ring appeared as a crucial moiety to maintain a broad scope of activities against different Gram-positive bacteria. Further modifications were performed to simplify the structure of the natural product and assess the role of its tail, resulting in an enhanced in vitro performance. Analogue 25, with the thiazole-containing macrocycle and a 4-aminocyclohexane-1-carboxylic acid moiety in place of the pentapeptidic tail, was identified as a much more potent analogue, capable of overcoming the absence of the thiazoline ring and performing extraordinarily well against all strains tested.,This is the first library of thiopeptide analogues produced by chemical synthesis alone, which demonstrates the robustness and convenience of the synthetic strategy used.

  DOI：

  10.1021/jm500062g
• 作为产物：
  描述：

  L-苯丙氨酰胺盐酸盐 在 劳森试剂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (S)-N-(allyloxycarbonyl)phenylalanine thioamide
  参考文献：
  名称：

  Dissecting the Structure of Thiopeptides: Assessment of Thiazoline and Tail Moieties of Baringolin and Antibacterial Activity Optimization

  摘要：

  Several analogues of baringolin (1) were prepared to evaluate the role of its characteristic thiazoline ring and pentapeptidic tail with the aim of defining structure activity relationships for these moieties. The thiazoline ring appeared as a crucial moiety to maintain a broad scope of activities against different Gram-positive bacteria. Further modifications were performed to simplify the structure of the natural product and assess the role of its tail, resulting in an enhanced in vitro performance. Analogue 25, with the thiazole-containing macrocycle and a 4-aminocyclohexane-1-carboxylic acid moiety in place of the pentapeptidic tail, was identified as a much more potent analogue, capable of overcoming the absence of the thiazoline ring and performing extraordinarily well against all strains tested.,This is the first library of thiopeptide analogues produced by chemical synthesis alone, which demonstrates the robustness and convenience of the synthetic strategy used.

  DOI：

  10.1021/jm500062g

文献信息

• [EN] DOLASTATIN 10 ANALOG<br/>[FR] ANALOGUE DE DOLASTATINE 10
  申请人：ARIEL SCIENT INNOVATIONS LTD

  公开号：WO2021084532A1

  公开（公告）日：2021-05-06

  Provided herein is a dolastatin 10 analog, useful for preparing conjugates thereof with targeting, diagnostic, imaging and other moieties. Also provided are the conjugates and uses thereof.

  本文提供了一种dolastatin 10类似物，可用于与靶向、诊断、成像和其他基团结合制备共轭物。还提供了这些共轭物及其用途。