6-[3-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-1-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid | 1351349-48-8

• 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-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-1-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
• CAS: 1351349-48-8
• 化学式: C₂₄H₂₉N₃O₅
• 分子量: 439.511
• InChiKey: GJMQMDHVIGCBGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  92.08
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-[3-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-1-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid 在 甲醇 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 26.5h， 生成 9-deoxo-4''-O-(3-{4-[3-(1-ethyl-3-carboxy-1,4-dihydro-4-oxo-quinolin-6-yl)prop-2-ynyl]piperazin-1-yl}propionyl)-9a,11-O-dimethyl-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Synthesis of macrolones with central piperazine ring in the linker and its influence on antibacterial activity

  摘要：

  Three macrolides, clarithromycin, azithromycin and 11-O-Me-azithromycin have been selected for the construction of a series of new macrolone derivatives. Quinolone-linker intermediates are prepared by Sonogashira-type C(6)-alkynylation of 6-iodoquinolone precursors. The final macrolones, differing by macrolide moiety and substituents at the position N-1 of the quinolone or by the presence of an ethyl ester or free acid on the quinolone unit attached via a linker.The linker comprises of a central piperazine ring bonded to the 4 ''-O position of cladinose by 3-carbon ester or ether functionality. Modifications of the linker did not improve antibacterial properties compared to the previously reported macrolone compounds. Linker flexibility seems to play an important role for potency against macrolide resistant respiratory pathogens. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.010
• 作为产物：
  描述：

  4-(2-丙炔)哌嗪-1-羧酸叔丁酯 、 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 6-[3-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-1-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Synthesis of macrolones with central piperazine ring in the linker and its influence on antibacterial activity

  摘要：

  Three macrolides, clarithromycin, azithromycin and 11-O-Me-azithromycin have been selected for the construction of a series of new macrolone derivatives. Quinolone-linker intermediates are prepared by Sonogashira-type C(6)-alkynylation of 6-iodoquinolone precursors. The final macrolones, differing by macrolide moiety and substituents at the position N-1 of the quinolone or by the presence of an ethyl ester or free acid on the quinolone unit attached via a linker.The linker comprises of a central piperazine ring bonded to the 4 ''-O position of cladinose by 3-carbon ester or ether functionality. Modifications of the linker did not improve antibacterial properties compared to the previously reported macrolone compounds. Linker flexibility seems to play an important role for potency against macrolide resistant respiratory pathogens. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.010