| 1248571-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1248571-16-5
• 化学式: C₆₀H₉₃N₃O₁₈
• 分子量: 1144.41
• InChiKey: CVWDKCKKFXIGAM-DHMYQFRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  81.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  260.75
• 氢给体数：
  4.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  在 甲醇 作用下， 反应 12.0h， 以33 mg的产率得到6-[3-[5-[(2S,3S,4R,6R)-6-[[(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-1-oxa-6-azacyclopentadec-13-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl]oxy-5-oxopentoxy]prop-1-ynyl]-1-ethyl-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile

  摘要：

  Two series of clarithromycin and azithromycin derivatives with terminal 6-alkylquinolone-3-carboxylic unit with central ether bond in the linker were prepared and tested for antimicrobial activity. Quinolonelinker intermediates were prepared by Sonogashira-type C(6)-alkynylation of 6-iodo-quinolone precursors. In the last step, 400 site-selective acylation of 2'-protected macrolides was completed with the EDC reagent, which selectively activated a terminal, aliphatic carboxylic group in dicarboxylic intermediates. Antimicrobial activity of the new series of macrolones is discussed. The most potent compound, 4"-O-{6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydroquinolin-6-yl)-propoxy]-hexanoyl}-azithromycin (10), is highly active against bacterial respiratory pathogens resistant to macrolide antibiotics and represents a promising lead for further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.048
• 作为产物：
  描述：

  6-[3-(4-carboxy-butoxy)-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 、 2'-O-acetylazithromycin 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以750 mg的产率得到
  参考文献：
  名称：

  6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile

  摘要：

  Two series of clarithromycin and azithromycin derivatives with terminal 6-alkylquinolone-3-carboxylic unit with central ether bond in the linker were prepared and tested for antimicrobial activity. Quinolonelinker intermediates were prepared by Sonogashira-type C(6)-alkynylation of 6-iodo-quinolone precursors. In the last step, 400 site-selective acylation of 2'-protected macrolides was completed with the EDC reagent, which selectively activated a terminal, aliphatic carboxylic group in dicarboxylic intermediates. Antimicrobial activity of the new series of macrolones is discussed. The most potent compound, 4"-O-{6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydroquinolin-6-yl)-propoxy]-hexanoyl}-azithromycin (10), is highly active against bacterial respiratory pathogens resistant to macrolide antibiotics and represents a promising lead for further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.048