[(2S,5R,6S)-2-[(S)-[(3aR,4S,6R,6aR)-2,2-diethyl-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxy-[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-5-(hydroxymethyl)-1,4-dimethyl-3-oxo-1,4-diazepan-6-yl] hexadecanoate | 1004750-99-5

• 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: [(2S,5R,6S)-2-[(S)-[(3aR,4S,6R,6aR)-2,2-diethyl-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxy-[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-5-(hydroxymethyl)-1,4-dimethyl-3-oxo-1,4-diazepan-6-yl] hexadecanoate
• CAS: 1004750-99-5
• 化学式: C₅₁H₈₅N₅O₁₅
• 分子量: 1008.26
• InChiKey: LFSSAUDIYDJCHF-SQTYENROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  71
• 可旋转键数：
  28
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  222
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  在 氟化铵 作用下， 以 甲醇 为溶剂， 生成 [(2S,5R,6S)-2-[(S)-[(3aR,4S,6R,6aR)-2,2-diethyl-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxy-[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-5-(hydroxymethyl)-1,4-dimethyl-3-oxo-1,4-diazepan-6-yl] hexadecanoate
  参考文献：
  名称：

  Synthesis of Caprazamycin Analogues and Their Structure−Activity Relationship for Antibacterial Activity

  摘要：

  Synthesis of palmitoyl caprazol 7, which possesses a simple fatty acyl side chain at the 3"'-position of the diazepanone moiety, was carried out and their antibacterial activity was evaluated. The key elements of our approach include the improved synthesis of the key 5'-p-0-aminoribosyl-glycyluridine derivative, installation of the palmitoyl side chain to the cyclization precursor, and the construction of the diazepanone by an intramolecular reductive amination. The second generation synthesis of (+)-caprazol was also established. Palmitoyl caprazol 7 exhibited antibacterial activity against Mycobacterium smegmatis ATCC607 (MIC = 6.25 mu g/mL) with potency similar to that of the caprazamycins (CPZs). Palmitoyl caprazol 7 and N-6'-desmethyl palmitoyl caprazol 28 also exhibited antibacterial activity against drug-resistant bacteria including methyciline-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE) strains (MIC = 3.13-12.5 mu g/mL).

  DOI：

  10.1021/jo702264e