4"-O-[tans-β-(3,4-dimethoxyphenyl)acrylamido]carbamoyl-azithromycin 11,12-cyclic carbonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4"-O-[tans-β-(3,4-dimethoxyphenyl)acrylamido]carbamoyl-azithromycin 11,12-cyclic carbonate
• 英文别名: [(2S,3S,4R,6R)-6-[[(1R,2R,5R,6S,7S,8R,9R,11R,14R,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-hydroxy-1,5,7,9,11,13,14-heptamethyl-4,17-dioxo-3,16,18-trioxa-13-azabicyclo[13.3.0]octadecan-6-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl] N-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]carbamate
• 化学式: C₅₁H₈₂N₄O₁₇
• 分子量: 1023.23
• InChiKey: UHHCRANNRKCUGG-CKECKFGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  72.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  240.81
• 氢给体数：
  4.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  4"-O-[tans-β-(3,4-dimethoxyphenyl)acrylamido]carbamoyl-azithromycin 11,12-cyclic carbonate 、 4-甲氧基苄胺 在 吡啶盐酸盐 作用下， 反应 72.0h， 以66.2%的产率得到4"-O-[trans-β-(3,4-dimethoxyphenyl)acrylamido]carbamoyl-11-O-(4-methoxybenzyl)carbamoyl-azithromycin
  参考文献：
  名称：

  Synthesis and antibacterial activity of 4″-O-(trans-β-arylacrylamido)carbamoyl azithromycin analogs

  摘要：

  Novel 4 ''-O-(trans-beta-arylacrylamido)carbamoyl azithromycin analogs were designed, synthesized and evaluated for their antibacterial activity against nine significant pathogens using broth microdilution method. A majority of these derivatives maintained the activity of azithromycin against susceptible Streptococcus pyogenes and all the compounds demonstrated remarkably improved activity compared with the references against all the three phenotypes of resistant Streptococcus pneumoniae. In particular, compound 24 exhibited the most potent activity against susceptible Staphylococcus aureus (MIC = 0.5 mu g/mL), S. pneumoniae (MIC = 0.06 mu g/mL) and S. pyogenes (MIC = 0.25 mu g/mL). The most active compound 7 (MIC = 0.015 mu g/mL) against resistant S. pneumoniae expressing the mefA gene, exhibited 512 and 256-fold more potent activity than erythromycin and azithromycin, respectively. Compounds 28 (MIC = 0.5 mu g/mL), 29 (MIC = 0.25 mu g/mL) and 30 (MIC = 0.5 mu g/mL) demonstrated potent activity against resistant S. pneumoniae expressing the ermB gene, which were 256, 512 and 256-fold better than the references, respectively. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.020
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酰氯 在 甲醇 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 4"-O-[tans-β-(3,4-dimethoxyphenyl)acrylamido]carbamoyl-azithromycin 11,12-cyclic carbonate
  参考文献：
  名称：

  Synthesis and antibacterial activity of 4″-O-(trans-β-arylacrylamido)carbamoyl azithromycin analogs

  摘要：

  Novel 4 ''-O-(trans-beta-arylacrylamido)carbamoyl azithromycin analogs were designed, synthesized and evaluated for their antibacterial activity against nine significant pathogens using broth microdilution method. A majority of these derivatives maintained the activity of azithromycin against susceptible Streptococcus pyogenes and all the compounds demonstrated remarkably improved activity compared with the references against all the three phenotypes of resistant Streptococcus pneumoniae. In particular, compound 24 exhibited the most potent activity against susceptible Staphylococcus aureus (MIC = 0.5 mu g/mL), S. pneumoniae (MIC = 0.06 mu g/mL) and S. pyogenes (MIC = 0.25 mu g/mL). The most active compound 7 (MIC = 0.015 mu g/mL) against resistant S. pneumoniae expressing the mefA gene, exhibited 512 and 256-fold more potent activity than erythromycin and azithromycin, respectively. Compounds 28 (MIC = 0.5 mu g/mL), 29 (MIC = 0.25 mu g/mL) and 30 (MIC = 0.5 mu g/mL) demonstrated potent activity against resistant S. pneumoniae expressing the ermB gene, which were 256, 512 and 256-fold better than the references, respectively. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.020

文献信息

• Synthesis and antibacterial activity of 4″-O-(trans-β-arylacrylamido)carbamoyl azithromycin analogs
  作者：Mi Yan、Xiaodong Ma、Ruiqian Dong、Xin Li、Can Zhao、Zhenzhen Guo、Yan Shen、Fang Liu、Ruixin Ma、Shutao Ma

  DOI：10.1016/j.ejmech.2015.09.020

  日期：2015.10

  Novel 4 ''-O-(trans-beta-arylacrylamido)carbamoyl azithromycin analogs were designed, synthesized and evaluated for their antibacterial activity against nine significant pathogens using broth microdilution method. A majority of these derivatives maintained the activity of azithromycin against susceptible Streptococcus pyogenes and all the compounds demonstrated remarkably improved activity compared with the references against all the three phenotypes of resistant Streptococcus pneumoniae. In particular, compound 24 exhibited the most potent activity against susceptible Staphylococcus aureus (MIC = 0.5 mu g/mL), S. pneumoniae (MIC = 0.06 mu g/mL) and S. pyogenes (MIC = 0.25 mu g/mL). The most active compound 7 (MIC = 0.015 mu g/mL) against resistant S. pneumoniae expressing the mefA gene, exhibited 512 and 256-fold more potent activity than erythromycin and azithromycin, respectively. Compounds 28 (MIC = 0.5 mu g/mL), 29 (MIC = 0.25 mu g/mL) and 30 (MIC = 0.5 mu g/mL) demonstrated potent activity against resistant S. pneumoniae expressing the ermB gene, which were 256, 512 and 256-fold better than the references, respectively. (C) 2015 Elsevier Masson SAS. All rights reserved.