methyl 2-((4S,7S,10S)-10-(2-((R)-2-((R)-3-(benzyloxy)-2-(N-methylpalmitamido)propanamido)propanamido)-N-methylacetamido)-16,26-dimethoxy-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-yl)acetate | 1458631-92-9

• 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: methyl 2-((4S,7S,10S)-10-(2-((R)-2-((R)-3-(benzyloxy)-2-(N-methylpalmitamido)propanamido)propanamido)-N-methylacetamido)-16,26-dimethoxy-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-yl)acetate
• CAS: 1458631-92-9
• 化学式: C₅₇H₈₂N₆O₁₁
• 分子量: 1027.31
• InChiKey: RDBLIKMUNNNPKD-URTKAZRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  74.0
• 可旋转键数：
  29.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  211.01
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 2-((4S,7S,10S)-10-(2-((R)-2-((R)-3-(benzyloxy)-2-(N-methylpalmitamido)propanamido)propanamido)-N-methylacetamido)-16,26-dimethoxy-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-yl)acetate 在 N-甲基吗啉 、 三甲基氢氧化锡 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成
  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：

  methyl (8S,11S,14S)-3,18-dimethoxy-11-methyl-14-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-10,13-dioxo-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-carboxylate 在 N-甲基吗啉 、 水 、 silver trifluoroacetate 、 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 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 31.17h， 生成 methyl 2-((4S,7S,10S)-10-(2-((R)-2-((R)-3-(benzyloxy)-2-(N-methylpalmitamido)propanamido)propanamido)-N-methylacetamido)-16,26-dimethoxy-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-yl)acetate
  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