(8S,11S,14S)-14-[[2-[[(2R)-2-[[(2R)-2-[hexadecanoyl(methyl)amino]-3-phenylmethoxypropanoyl]amino]propanoyl]amino]acetyl]-methylamino]-18-hydroxy-11-methyl-10,13-dioxo-3-phenylmethoxy-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-carboxylic acid | 1458631-90-7

• 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: (8S,11S,14S)-14-[[2-[[(2R)-2-[[(2R)-2-[hexadecanoyl(methyl)amino]-3-phenylmethoxypropanoyl]amino]propanoyl]amino]acetyl]-methylamino]-18-hydroxy-11-methyl-10,13-dioxo-3-phenylmethoxy-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-carboxylic acid
• CAS: 1458631-90-7
• 化学式: C₆₀H₈₀N₆O₁₁
• 分子量: 1061.33
• InChiKey: IADDYKQDYNYEDJ-VGIWLEGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  77
• 可旋转键数：
  29
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  233
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (8S,11S,14S)-14-[[2-[[(2R)-2-[[(2R)-2-[hexadecanoyl(methyl)amino]-3-phenylmethoxypropanoyl]amino]propanoyl]amino]acetyl]-methylamino]-18-hydroxy-11-methyl-10,13-dioxo-3-phenylmethoxy-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-carboxylic acid 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 甲酸 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.17h， 生成 (8S,11S,14S)-N-(2,3-dihydroxypropyl)-14-[[2-[[(2R)-2-[[(2R)-2-[hexadecanoyl(methyl)amino]-3-hydroxypropanoyl]amino]propanoyl]amino]acetyl]-methylamino]-3,18-dihydroxy-11-methyl-10,13-dioxo-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-carboxamide
  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：

  在 碳酸氢钠 、 三甲基氢氧化锡 、 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 、 1,2-二氯乙烷 为溶剂， 反应 30.0h， 生成 (8S,11S,14S)-14-[[2-[[(2R)-2-[[(2R)-2-[hexadecanoyl(methyl)amino]-3-phenylmethoxypropanoyl]amino]propanoyl]amino]acetyl]-methylamino]-18-hydroxy-11-methyl-10,13-dioxo-3-phenylmethoxy-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