9-deoxo-4''-O-(3-{4-[3-(1-ethyl-3-ethoxycarbonyl-1,4-dihydro-4-oxo-quinolin-6-yl)prop-2-ynyl]piperazin-1-yl}propionyl)-9a,11-O-dimethyl-9a-aza-9a-homoerythromycin A

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-deoxo-4''-O-(3-{4-[3-(1-ethyl-3-ethoxycarbonyl-1,4-dihydro-4-oxo-quinolin-6-yl)prop-2-ynyl]piperazin-1-yl}propionyl)-9a,11-O-dimethyl-9a-aza-9a-homoerythromycin A
• 英文别名: 4"-O-(3-{4-[3-(3-ethoxycarbonyl-1-ethyl-4-oxo-1,4-dihydro-quinolin-6-yl)-prop-2-ynyl]-piperazin-1-yl}-propionyl)-11-O-methyl-azithromycin；ethyl 6-[3-[4-[3-[(2S,3S,4R,6R)-6-[[(2R,3R,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,10-dihydroxy-4-methoxy-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-3-oxopropyl]piperazin-1-yl]prop-1-ynyl]-1-ethyl-4-oxoquinoline-3-carboxylate
• 化学式: C₆₃H₁₀₁N₅O₁₆
• 分子量: 1184.52
• InChiKey: AXQDYIKVSIUUGP-OQQXUGEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  84
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  228
• 氢给体数：
  3
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  9-deoxo-4''-O-(3-{4-[3-(1-ethyl-3-ethoxycarbonyl-1,4-dihydro-4-oxo-quinolin-6-yl)prop-2-ynyl]piperazin-1-yl}propionyl)-9a,11-O-dimethyl-9a-aza-9a-homoerythromycin A 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 20.0h， 以12%的产率得到9-deoxo-4''-O-(3-{4-[3-(1-ethyl-3-ethoxycarbonyl-1,4-dihydro-4-oxo-quinolin-6-yl)propyl]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：

  11-O-Me-2'-O-acetyl-azithromycin 在 甲醇 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 生成 9-deoxo-4''-O-(3-{4-[3-(1-ethyl-3-ethoxycarbonyl-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

文献信息

• Synthesis of macrolones with central piperazine ring in the linker and its influence on antibacterial activity
  作者：Samra Kapić、Hana Čipčić Paljetak、Ivana Palej Jakopović、Andrea Fajdetić、Marina Ilijaš、Vlado Štimac、Karmen Brajša、David J. Holmes、John Berge、Sulejman Alihodžić

  DOI：10.1016/j.bmc.2011.07.010

  日期：2011.12

  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.