6-[3-(4-carboxy-butoxy)-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 1248571-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-[3-(4-carboxy-butoxy)-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 6-[3-(4-Carboxybutoxy)prop-1-ynyl]-1-ethyl-4-oxoquinoline-3-carboxylic acid
• CAS: 1248571-05-2
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: DJMCHDJEDKQICE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[3-(4-carboxy-butoxy)-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 、 2'-O-acetyl-6-O-methylerythromycin A 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490 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
• 作为产物：
  描述：

  6-[3-(4-ethoxycarbonyl-butoxy)-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 以185 mg的产率得到6-[3-(4-carboxy-butoxy)-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-quinoline-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

文献信息

• 6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile
  作者：Samra Kapić、Hana Čipčić Paljetak、Sulejman Alihodžić、Roberto Antolović、Vesna Eraković Haber、Richard L. Jarvest、David J. Holmes、John P. Broskey、Eric Hunt

  DOI：10.1016/j.bmc.2010.06.048

  日期：2010.9

  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.