9-deoxo-9a-N-(N'-isopropylcarbamoyl)-9a-aza-9a-homoerythronolide A

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-deoxo-9a-N-(N'-isopropylcarbamoyl)-9a-aza-9a-homoerythronolide A
• 英文别名: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10,11,13-pentahydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-N-propan-2-yl-1-oxa-6-azacyclopentadecane-6-carboxamide
• 化学式: C₂₅H₄₈N₂O₈
• 分子量: 504.665
• InChiKey: SWUAIOHUHNCVFE-RKPLXFHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  160
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  10-dihydro-10-deoxo-11-azaerythronolide A 、 异氰酸异丙酯 以 甲苯 为溶剂， 反应 0.5h， 以77.2%的产率得到9-deoxo-9a-N-(N'-isopropylcarbamoyl)-9a-aza-9a-homoerythronolide A
  参考文献：
  名称：

  Azalides: synthesis and antibacterial activity of novel 9a-N-(N′-substituted carbamoyl and thiocarbamoyl) derivatives of 9-deoxo-9a-aza-9a-homoerythromycin A

  摘要：

  A series of 9a-N-(N'-substituted carbamoyl and thiocarbamoyl) derivatives of 9-deoxo-9a-aza-9a-homoerythromycin A was synthesized and structurally characterized by spectroscopic methods and X-ray crystallographic analysis. The new compounds were evaluated in vitro against a panel of Gram-positive and Gram-negative bacteria and their antibacterial activities compared with those of the parent 9a-amine 2 and azithromycin 3. The results indicate that this type of structural modification offers no benefit over 2 and that the potency of the majority of these compounds in vitro decreased in comparison with 3. Among the tested azalides, the N'-isopropylcarbamoyl derivative 4 and the N'-benzylthiocarbamoyl derivative 12 showed the most potent antibacterial in vitro activity.

  DOI：

  10.1016/0223-5234(96)88256-0

文献信息

• Azalides: synthesis and antibacterial activity of novel 9a-N-(N′-substituted carbamoyl and thiocarbamoyl) derivatives of 9-deoxo-9a-aza-9a-homoerythromycin A
  作者：N Kujundić、G Kobrehel、Z Banić、Z Kelnerić、B Koić-Prodić

  DOI：10.1016/0223-5234(96)88256-0

  日期：1995.1

  A series of 9a-N-(N'-substituted carbamoyl and thiocarbamoyl) derivatives of 9-deoxo-9a-aza-9a-homoerythromycin A was synthesized and structurally characterized by spectroscopic methods and X-ray crystallographic analysis. The new compounds were evaluated in vitro against a panel of Gram-positive and Gram-negative bacteria and their antibacterial activities compared with those of the parent 9a-amine 2 and azithromycin 3. The results indicate that this type of structural modification offers no benefit over 2 and that the potency of the majority of these compounds in vitro decreased in comparison with 3. Among the tested azalides, the N'-isopropylcarbamoyl derivative 4 and the N'-benzylthiocarbamoyl derivative 12 showed the most potent antibacterial in vitro activity.