EtO-Thiazole-Ala-NMeBoc | 1414375-86-2

• 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-NMeBoc
• 英文别名: Boc-NMe-Ala-Th-OEt；ethyl 2-[(1S)-1-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]-1,3-thiazole-4-carboxylate
• CAS: 1414375-86-2
• 化学式: C₁₄H₂₂N₂O₄S
• 分子量: 314.406
• InChiKey: NYWFATSRYKQRGV-VIFPVBQESA-N

物化性质

• 沸点：
  387.4±25.0 °C(predicted)
• 密度：
  1.164±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  97
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  EtO-Thiazole-Ala-NMeBoc 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 EtO-Thiazole-Ala-NMe-Val-NH2
  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：

  N-^tBOC-N-methyl-L-alanine methyl ester 在 劳森试剂 、 吡啶 、 ammonium hydroxide 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 3.5h， 生成 EtO-Thiazole-Ala-NMeBoc
  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