San B 9 | 1414375-76-0

• 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: San B 9
• 英文别名: (6S,12S,19S,22S,25S)-12-benzyl-19-methyl-22-propan-2-yl-33-oxa-4,17-dithia-10,13,20,23,29,34,35,36-octazahexacyclo[29.2.1.12,5.115,18.06,10.025,29]hexatriaconta-1(34),2,5(36),15,18(35),31-hexaene-11,14,21,24,30-pentone
• CAS: 1414375-76-0
• 化学式: C₃₆H₄₀N₈O₆S₂
• 分子量: 744.896
• InChiKey: IGBCJTZPMBOPDT-RPEPFXESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  52
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  236
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  MeO-Oxazole-Thiazole-Pro-NH 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 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 、 lithium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 San B 9
  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

文献信息

• Synthesis, Structure–Activity Analysis, and Biological Evaluation of Sanguinamide B Analogues
  作者：Hendra Wahyudi、Worawan Tantisantisom、Xuechao Liu、Deborah M. Ramsey、Erinprit K. Singh、Shelli R. McAlpine

  DOI：10.1021/jo3017499

  日期：2012.12.7

  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.