methyl (4S,7S,10S)-26-(benzyloxy)-16-(2-(benzyloxy)ethoxy)-10-((tert-butoxycarbonyl)(methyl)amino)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate | 1458632-00-2

• 分子结构分类: 有机化合物
• 英文名称: methyl (4S,7S,10S)-26-(benzyloxy)-16-(2-(benzyloxy)ethoxy)-10-((tert-butoxycarbonyl)(methyl)amino)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate
• CAS: 1458632-00-2
• 化学式: C₄₃H₄₉N₃O₉
• 分子量: 751.877
• InChiKey: UGKGVUZMXKCNAB-AGIKJSORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  55.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  141.73
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (4S,7S,10S)-26-(benzyloxy)-16-(2-(benzyloxy)ethoxy)-10-((tert-butoxycarbonyl)(methyl)amino)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate 在 碳酸氢钠 、 三氟乙酸 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 methyl (4S,7S,10S)-26-(benzyloxy)-10-(2-((R)-2-((R)-3-(benzyloxy)-2-(N-methylpalmitamido)propanamido)propanamido)-N-methylacetamido)-16-(2-(benzyloxy)ethoxy)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate
  参考文献：
  名称：

  Efforts toward broadening the spectrum of arylomycin antibiotic activity

  摘要：

  New antibiotics are needed, and one source may be 'latent' antibiotics, natural products whose once broad-spectrum activity is currently limited by the evolution of resistance in nature. We have identified a potential class of latent antibiotics, the arylomycins, which are lipopeptides with a C-terminal macrocycle that target signal peptidase and whose spectrum is limited by a resistance-conferring mutation in many bacteria. Herein, we report the synthesis and evaluation of several arylomycin derivatives, and demonstrate that both C-terminal homologation with a glycyl aldehyde and addition of a positive charge to the macrocycle increase the activity and spectrum of the arylomycin scaffold. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.026
• 作为产物：
  描述：

  1-苄氧基-2-碘乙烷 、 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以69%的产率得到methyl (4S,7S,10S)-26-(benzyloxy)-16-(2-(benzyloxy)ethoxy)-10-((tert-butoxycarbonyl)(methyl)amino)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate
  参考文献：
  名称：

  Efforts toward broadening the spectrum of arylomycin antibiotic activity

  摘要：

  New antibiotics are needed, and one source may be 'latent' antibiotics, natural products whose once broad-spectrum activity is currently limited by the evolution of resistance in nature. We have identified a potential class of latent antibiotics, the arylomycins, which are lipopeptides with a C-terminal macrocycle that target signal peptidase and whose spectrum is limited by a resistance-conferring mutation in many bacteria. Herein, we report the synthesis and evaluation of several arylomycin derivatives, and demonstrate that both C-terminal homologation with a glycyl aldehyde and addition of a positive charge to the macrocycle increase the activity and spectrum of the arylomycin scaffold. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.026