2',4"-bis(trimethylsilyl)-6-O-methylerythromycin A 9-O-(1-ethoxycyclohexyl)oxime | 756821-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',4"-bis(trimethylsilyl)-6-O-methylerythromycin A 9-O-(1-ethoxycyclohexyl)oxime
• CAS: 756821-72-4
• 化学式: C₅₂H₁₀₀N₂O₁₄Si₂
• 分子量: 1033.54
• InChiKey: STKXAGHBFYEYRB-LIWBZCTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  70.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  174.66
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2',4"-bis(trimethylsilyl)-6-O-methylerythromycin A 9-O-(1-ethoxycyclohexyl)oxime 在 吡啶 、 盐酸 、 potassium tert-butylate 、 水 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.17h， 生成 [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1R,2R,5R,6S,7S,8R,9R,11R,12E,13S,14R)-2-ethyl-6-hydroxy-9-methoxy-1,5,7,9,11,13-hexamethyl-4,16-dioxo-12-prop-2-ynoxyimino-3,15,17-trioxabicyclo[12.3.0]heptadecan-8-yl]oxy]-6-methyloxan-3-yl] acetate
  参考文献：
  名称：

  Synthesis, antibacterial activity and docking of 14-membered 9-O-(3-arylalkyl) oxime 11,12-cyclic carbonate ketolides

  摘要：

  A series of 9-O-(3-aryl-2-propargyl)oxime ketolides 8 was synthesized and evaluated for in vitro antibacterial activity. Among 8, 8b-8d, and 8h-8l displayed dramatically improved potency against inducibly MLSB-resistant and efflux-resistant pathogens as compared to clarithromycin and azithromycin. Especially, 8i (Ar=4-isoquinolyl) possessed an MIC of 0.064 mu g/mL against constitutively MLSB-resistant Streptococcus pneumoniae, and MICs of 0.032-0.064 mu g/mL against methicillin-resistant Staphylococcus aureus and methicillin-resistant Staphylococcus hominis. The analog 10 with a propyl linker was less effective than both the corresponding 8 and 9 containing propynyl and propenyl linkers. A docking study was performed to gain insight into the binding mode of series 8 and 9 and to rationalize the disparity found in the SAR of 8 and 9. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.054