N,N'-di(demethyl)azithromycin 2',3'-carbamate-11,12-carbonate | 1063590-52-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: N,N'-di(demethyl)azithromycin 2',3'-carbamate-11,12-carbonate
• 英文别名: (1R,2R,5R,6S,7S,8R,9R,11R,14R,15R)-8-[[(3aR,4S,6R,7aS)-1,6-dimethyl-2-oxo-4,6,7,7a-tetrahydro-3aH-pyrano[4,3-d][1,3]oxazol-4-yl]oxy]-2-ethyl-9-hydroxy-6-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-1,5,7,9,11,14-hexamethyl-3,16,18-trioxa-13-azabicyclo[13.3.0]octadecane-4,17-dione
• CAS: 1063590-52-2
• 化学式: C₃₈H₆₄N₂O₁₄
• 分子量: 772.931
• InChiKey: UOVZFCNFVZZMHN-LHICCUKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  190
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N,N'-di(demethyl)azithromycin 2',3'-carbamate-11,12-carbonate 在 甲酸 作用下， 以 氯仿 为溶剂， 反应 22.0h， 以136 mg的产率得到N'-demethylazithromycin 2',3'-carbamate-11,12-carbonate
  参考文献：
  名称：

  Preparation and antibacterial activity of cyclic 2′,3′-carbamate derivatives of azithromycin

  摘要：

  In a study of the importance of a basic amino function in erythromycin derived antibiotics, N '-demethylazithromycin 2 ',3 '-carbamate-11, 12-carbonate has been prepared in six steps from (9E)-erythromycin A 9-oxime. Reactions with phosgene provided a cyclic carbonate from the vicinal 11,12-diol, and a cyclic 2 ',3 '-carbamate from the vicinal dimethylamino-alcohol moiety of the desosamine sugar. Further transformations provided N,N '-di(demethyl)azithromycin 2 ',3 '-carbamate-11, 12-carbonate N-methylated at position 9a. The activity of the oxime was reduced in comparison with the parent azithromycin. Hence the N,N-dimethylamino group in the desosamine sugar is important for good antibacterial activity. The course of the phosgene reactions has been verified by an X-ray analysis. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.013
• 作为产物：
  描述：

  9,9a-anhydro-N,N'-di(demethyl)azithromycin-6,9-hemiketal 2',3'-carbamate-11,12-carbonate 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 20.0 ℃ 、7.0 MPa 条件下， 反应 2.0h， 生成 N,N'-di(demethyl)azithromycin 2',3'-carbamate-11,12-carbonate
  参考文献：
  名称：

  Preparation and antibacterial activity of cyclic 2′,3′-carbamate derivatives of azithromycin

  摘要：

  In a study of the importance of a basic amino function in erythromycin derived antibiotics, N '-demethylazithromycin 2 ',3 '-carbamate-11, 12-carbonate has been prepared in six steps from (9E)-erythromycin A 9-oxime. Reactions with phosgene provided a cyclic carbonate from the vicinal 11,12-diol, and a cyclic 2 ',3 '-carbamate from the vicinal dimethylamino-alcohol moiety of the desosamine sugar. Further transformations provided N,N '-di(demethyl)azithromycin 2 ',3 '-carbamate-11, 12-carbonate N-methylated at position 9a. The activity of the oxime was reduced in comparison with the parent azithromycin. Hence the N,N-dimethylamino group in the desosamine sugar is important for good antibacterial activity. The course of the phosgene reactions has been verified by an X-ray analysis. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.013

文献信息

• Preparation and antibacterial activity of cyclic 2′,3′-carbamate derivatives of azithromycin
  作者：Audun Heggelund、Christian Rømming、Kjell Undheim

  DOI：10.1016/j.ejmech.2007.10.013

  日期：2008.8

  In a study of the importance of a basic amino function in erythromycin derived antibiotics, N '-demethylazithromycin 2 ',3 '-carbamate-11, 12-carbonate has been prepared in six steps from (9E)-erythromycin A 9-oxime. Reactions with phosgene provided a cyclic carbonate from the vicinal 11,12-diol, and a cyclic 2 ',3 '-carbamate from the vicinal dimethylamino-alcohol moiety of the desosamine sugar. Further transformations provided N,N '-di(demethyl)azithromycin 2 ',3 '-carbamate-11, 12-carbonate N-methylated at position 9a. The activity of the oxime was reduced in comparison with the parent azithromycin. Hence the N,N-dimethylamino group in the desosamine sugar is important for good antibacterial activity. The course of the phosgene reactions has been verified by an X-ray analysis. (c) 2007 Elsevier Masson SAS. All rights reserved.