methyl (4S,7S,10S)-26-(benzyloxy)-10-(2-((R)-2-((R)-3-(benzyloxy)-2-(N-methylpalmitamido)propanamido)propanamido)-N-methylacetamido)-16-(2-(((benzyloxy)carbonyl)amino)ethoxy)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate | 1458631-99-6

• 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 (4S,7S,10S)-26-(benzyloxy)-10-(2-((R)-2-((R)-3-(benzyloxy)-2-(N-methylpalmitamido)propanamido)propanamido)-N-methylacetamido)-16-(2-(((benzyloxy)carbonyl)amino)ethoxy)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate
• CAS: 1458631-99-6
• 化学式: C₇₁H₉₃N₇O₁₃
• 分子量: 1252.56
• InChiKey: VPSDJGFLYBFUQK-BBJCQKNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  91.0
• 可旋转键数：
  35.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  249.34
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl (4S,7S,10S)-26-(benzyloxy)-10-(2-((R)-2-((R)-3-(benzyloxy)-2-(N-methylpalmitamido)propanamido)propanamido)-N-methylacetamido)-16-(2-(((benzyloxy)carbonyl)amino)ethoxy)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate 在 三甲基氢氧化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 (8S,11S,14S)-14-[[2-[[(2R)-2-[[(2R)-2-[hexadecanoyl(methyl)amino]-3-phenylmethoxypropanoyl]amino]propanoyl]amino]acetyl]-methylamino]-11-methyl-10,13-dioxo-3-phenylmethoxy-18-[2-(phenylmethoxycarbonylamino)ethoxy]-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-carboxylic acid
  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)-11-methyl-14-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-10,13-dioxo-3-phenylmethoxy-18-[2-(phenylmethoxycarbonylamino)ethoxy]-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-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)carbonyl)amino)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