(1R,2R,5R,7R,8R,9R,11R,12E,13S,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-12-(3-quinolin-3-ylpropoxyimino)-3,15,17-trioxabicyclo[12.3.0]heptadecane-4,6,16-trione | 1422364-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,5R,7R,8R,9R,11R,12E,13S,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-12-(3-quinolin-3-ylpropoxyimino)-3,15,17-trioxabicyclo[12.3.0]heptadecane-4,6,16-trione
• CAS: 1422364-45-1
• 化学式: C₄₃H₆₃N₃O₁₁
• 分子量: 797.987
• InChiKey: FHODXLUICIGDBI-AKLJTMLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  57
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  3-O-descladinosyl-3-keto-6-O-methylerythromycin A 9-O-[3-(3'-quinolyl)-E-prop-2-enyl]oxime 11,12-cyclic carbonate 在 甲酸 、 palladium 10% on activated carbon 、 氢气 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以18.7%的产率得到(1R,2R,5R,7R,8R,9R,11R,12E,13S,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-12-(3-quinolin-3-ylpropoxyimino)-3,15,17-trioxabicyclo[12.3.0]heptadecane-4,6,16-trione
  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