EtO-Thiazole-Ala-NMeH | 1421234-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: EtO-Thiazole-Ala-NMeH
• CAS: 1421234-94-7
• 化学式: C₉H₁₄N₂O₂S
• 分子量: 214.288
• InChiKey: JBYHQOMWQNZNQP-LURJTMIESA-N

物化性质

• 沸点：
  286.1±20.0 °C(predicted)
• 密度：
  1.155±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  EtO-Thiazole-Ala-NMeH 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 苯甲醚 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 HO-Thiazole-Ala-NMe-Val-Pro-Oxazole-Thiazole-Pro-Leu-NHBoc
  参考文献：
  名称：

  Synthesis, Structure–Activity Analysis, and Biological Evaluation of Sanguinamide B Analogues

  摘要：

  We report the first synthesis of sanguinamide B analogues. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogues all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogues showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a "pseudoequatorial" position, and all other energy considerations are secondary.

  DOI：

  10.1021/jo3017499
• 作为产物：
  描述：

  EtO-Thiazole-Ala-NMeBoc 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到EtO-Thiazole-Ala-NMeH
  参考文献：
  名称：

  Synthesis, Structure–Activity Analysis, and Biological Evaluation of Sanguinamide B Analogues

  摘要：

  We report the first synthesis of sanguinamide B analogues. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogues all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogues showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a "pseudoequatorial" position, and all other energy considerations are secondary.

  DOI：

  10.1021/jo3017499