(1R,3R,6R,8R,9R,10R,12R,13S,17S)-methyl-9-((2S,3R,4S,6R)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yloxy)-3-ethyl-10-methoxy-6,8,10,12,15,15,17-heptamethyl-5,7-dioxo-3',5'-dihydro-4,14,16-trioxaspiro[bicyclo[11.3.1]heptadecane-2,4'-pyrazole]-3'-carboxylate | 1261067-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,6R,8R,9R,10R,12R,13S,17S)-methyl-9-((2S,3R,4S,6R)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yloxy)-3-ethyl-10-methoxy-6,8,10,12,15,15,17-heptamethyl-5,7-dioxo-3',5'-dihydro-4,14,16-trioxaspiro[bicyclo[11.3.1]heptadecane-2,4'-pyrazole]-3'-carboxylate
• 英文别名: methyl (1'R,3'R,6'R,8'R,9'R,10'R,12'R,13'S,17'S)-9'-[(2S,3R,4S,6R)-3-benzoyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-3'-ethyl-10'-methoxy-6',8',10',12',15',15',17'-heptamethyl-5',7'-dioxospiro[3,5-dihydropyrazole-4,2'-4,14,16-trioxabicyclo[11.3.1]heptadecane]-3-carboxylate
• CAS: 1261067-76-8
• 化学式: C₄₃H₆₅N₃O₁₂
• 分子量: 816.002
• InChiKey: BHMAXTVWVUMCEQ-OHWUBHQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  58
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (1R,3R,6R,8R,9R,10R,12R,13S,17S)-methyl-9-((2S,3R,4S,6R)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yloxy)-3-ethyl-10-methoxy-6,8,10,12,15,15,17-heptamethyl-5,7-dioxo-3',5'-dihydro-4,14,16-trioxaspiro[bicyclo[11.3.1]heptadecane-2,4'-pyrazole]-3'-carboxylate 在 4-甲基苯磺酸吡啶 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以81.9%的产率得到(6R,9R,11R,12R,13R,15R,16S,17S,18R)-methyl 12-((2S,3R,4S,6R)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yloxy)-6-ethyl-16,18-dihydroxy-13-methoxy-9,11,13,15,17-pentamethyl-8,10-dioxo-7-oxa-2,3-diazaspiro[4.13]octadec-3-ene-1-carboxylate
  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)-4-(dimethylamino)-2-((1R,3R,6R,8R,9R,10R,12R,13S,17S)-3-ethyl-10-methoxy-6,8,10,12,15,15,17-heptamethyl-2-methylene-5,7-dioxo-4,14,16-trioxabicyclo[11.3.1]heptadecan-9-yloxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate 、 重氮乙酸甲酯 以 1,2-二氯乙烷 为溶剂， 反应 25.0h， 以69.7%的产率得到(1R,3R,6R,8R,9R,10R,12R,13S,17S)-methyl-9-((2S,3R,4S,6R)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yloxy)-3-ethyl-10-methoxy-6,8,10,12,15,15,17-heptamethyl-5,7-dioxo-3',5'-dihydro-4,14,16-trioxaspiro[bicyclo[11.3.1]heptadecane-2,4'-pyrazole]-3'-carboxylate
  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.