2'-acetyl-4''-O-{6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydro-quinolin-6-yl)-prop-2-ynyloxy]-hexanoyl}-11-O-Me-azithromycin | 797815-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-acetyl-4''-O-{6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydro-quinolin-6-yl)-prop-2-ynyloxy]-hexanoyl}-11-O-Me-azithromycin
• 英文别名: 2'-acetyl-4"-O-{6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydro-quinolin-6-yl)-prop-2-ynyloxy]-hexanoyl}-11-O-Me-azithromycin
• CAS: 797815-95-3
• 化学式: C₆₂H₉₇N₃O₁₈
• 分子量: 1172.46
• InChiKey: STJXVBDCCMLHMZ-RGRPYVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  83.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  249.75
• 氢给体数：
  3.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  2'-acetyl-4''-O-{6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydro-quinolin-6-yl)-prop-2-ynyloxy]-hexanoyl}-11-O-Me-azithromycin 在 甲醇 作用下， 反应 12.0h， 以66 mg的产率得到4''-O-{6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydro-quinolin-6-yl)-propyn-2-yloxy]-hexanoyl}-11-O-methyl-azithromycin
  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：

  11-O-Me-2'-O-acetyl-azithromycin 、 6-[3-(5-carboxy-pentyloxy)-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 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， 反应 27.0h， 生成 2'-acetyl-4''-O-{6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydro-quinolin-6-yl)-prop-2-ynyloxy]-hexanoyl}-11-O-Me-azithromycin
  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