(2S,3R,4S,6R)-4-(dimethylamino)-2-((3R,4S,5S,6R,7R,9R,10S,11S,12R,14R)-14-ethyl-4,10,12-trihydroxy-7-methoxy-3,5,7,9,11-pentamethyl-13-methylene-2-oxooxacyclotetradecan-6-yloxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate | 1111873-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,6R)-4-(dimethylamino)-2-((3R,4S,5S,6R,7R,9R,10S,11S,12R,14R)-14-ethyl-4,10,12-trihydroxy-7-methoxy-3,5,7,9,11-pentamethyl-13-methylene-2-oxooxacyclotetradecan-6-yloxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate
• 英文别名: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,10S,11S,12R,14R)-14-ethyl-4,10,12-trihydroxy-7-methoxy-3,5,7,9,11-pentamethyl-13-methylidene-2-oxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] benzoate
• CAS: 1111873-42-7
• 化学式: C₃₇H₅₉NO₁₀
• 分子量: 677.876
• InChiKey: OZFXGOMUEUNMBK-QUFBVXBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,6R)-4-(dimethylamino)-2-((3R,4S,5S,6R,7R,9R,10S,11S,12R,14R)-14-ethyl-4,10,12-trihydroxy-7-methoxy-3,5,7,9,11-pentamethyl-13-methylene-2-oxooxacyclotetradecan-6-yloxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以91.3%的产率得到(2S,3R,4S,6R)-4-(dimethylamino)-2-((1R,3R,6R,7S,8S,9R,10R,12R,13S,17S)-3-ethyl-7-hydroxy-10-methoxy-6,8,10,12,15,15,17-heptamethyl-2-methylene-5-oxo-4,14,16-trioxabicyclo[11.3.1]heptadecan-9-yloxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate
  参考文献：
  名称：

  Synthesis and antibacterial activity of C-12 pyrazolinyl spiro ketolides

  摘要：

  A series of C-12 pyrazolinyl Spiro ketolide derivatives were designed and synthesized. The C-12 modifications involved replacing the natural C-12 methyl group in clarithromycin core with different pyrazolinyl spiros via chemical synthesis. Potential anti-bacterial activities against both erythromycin-susceptible and erythromycin-resistant bacteria were reported. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.060
• 作为产物：
  描述：

  [(2S,3R,4S,6R)-2-[[(1R,3R,6R,7S,8S,9R,10R,12R,13S,17S)-7-[(2R,4R,5S,6S)-5-benzoyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3-ethyl-10-methoxy-6,8,10,12,15,15,17-heptamethyl-2-methylidene-5-oxo-4,14,16-trioxabicyclo[11.3.1]heptadecan-9-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] benzoate 在 盐酸 、 水 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以85.2%的产率得到(2S,3R,4S,6R)-4-(dimethylamino)-2-((3R,4S,5S,6R,7R,9R,10S,11S,12R,14R)-14-ethyl-4,10,12-trihydroxy-7-methoxy-3,5,7,9,11-pentamethyl-13-methylene-2-oxooxacyclotetradecan-6-yloxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate
  参考文献：
  名称：

  Synthesis and antibacterial activity of C-12 pyrazolinyl spiro ketolides

  摘要：

  A series of C-12 pyrazolinyl Spiro ketolide derivatives were designed and synthesized. The C-12 modifications involved replacing the natural C-12 methyl group in clarithromycin core with different pyrazolinyl spiros via chemical synthesis. Potential anti-bacterial activities against both erythromycin-susceptible and erythromycin-resistant bacteria were reported. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.060

文献信息

• Synthesis and antibacterial activity of C-12 pyrazolinyl spiro ketolides
  作者：Lei Hu、Ping Lan、Qiu-Ling Song、Zhi-Jian Huang、Ping-Hua Sun、Chao Zhuo、Ying Wang、Shunian Xiao、Wei-Min Chen

  DOI：10.1016/j.ejmech.2010.09.060

  日期：2010.12

  A series of C-12 pyrazolinyl Spiro ketolide derivatives were designed and synthesized. The C-12 modifications involved replacing the natural C-12 methyl group in clarithromycin core with different pyrazolinyl spiros via chemical synthesis. Potential anti-bacterial activities against both erythromycin-susceptible and erythromycin-resistant bacteria were reported. (C) 2010 Elsevier Masson SAS. All rights reserved.