[(2S,3S,4R,6R)-6-[[(6R,7S,8R,10R,11R,12S,13S,14R)-7-amino-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-hydroxy-4,6,8,10,12,14-hexamethyl-15-oxo-1-oxa-4-azacyclopentadec-13-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl] N-[2-[ethyl-[(1S)-1-(2-methoxyphenyl)ethyl]amino]ethyl]carbamate | 497832-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,4R,6R)-6-[[(6R,7S,8R,10R,11R,12S,13S,14R)-7-amino-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-hydroxy-4,6,8,10,12,14-hexamethyl-15-oxo-1-oxa-4-azacyclopentadec-13-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl] N-[2-[ethyl-[(1S)-1-(2-methoxyphenyl)ethyl]amino]ethyl]carbamate
• CAS: 497832-06-1
• 化学式: C₄₉H₈₇N₅O₁₂
• 分子量: 938.256
• InChiKey: JQXSMTCOFYFISJ-ZDDRJOACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  66
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  196
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  (9S)-9-氨基-9-脱氧乙琥红霉素 在 咪唑 、 lithium hydroxide monohydrate 、 2,4,6-三氯苯甲酰氯 、 5% Pd/C 、 水 、 氢气 、 lead(IV) tetraacetate 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 239.75h， 生成 [(2S,3S,4R,6R)-6-[[(6R,7S,8R,10R,11R,12S,13S,14R)-7-amino-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-hydroxy-4,6,8,10,12,14-hexamethyl-15-oxo-1-oxa-4-azacyclopentadec-13-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl] N-[2-[ethyl-[(1S)-1-(2-methoxyphenyl)ethyl]amino]ethyl]carbamate
  参考文献：
  名称：

  Synthesis and structure–activity relationship of a novel class of 15-membered macrolide antibiotics known as ‘11a-azalides’

  摘要：

  Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide scaffolds with activities against resistant pathogens is urgently needed. An efficient method for reconstructing the erythromycin A macrolactone skeleton has been established. Based on this methodology, novel 15-membered macrolides, known as '11a-azalides', with substituents at the C12, C13, or C4 '' positions were synthesized and their antibacterial activities were evaluated. These derivatives showed promising antibacterial activities against erythromycin-resistant Streptococcus pneumoniae. Among them, the C4 '' substituted derivatives had the most potent activity against erythromycin-resistant S. pneumoniae. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.007