| 1383612-19-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• CAS: 1383612-19-8
• 化学式: C₄₅H₇₃N₃O₁₄
• 分子量: 880.086
• InChiKey: PWVKMKMLVNDWGU-IMWLQTJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  62.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  205.53
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  3'-N-demethyl-6-O-methyl-8a-aza-8a-homoerythromycin A 、 4-甲氧基苯基 异硫氰酸酯 在 三乙胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  N′-Substituted-2′-O,3′-N-carbonimidoyl Bridged Macrolides: Novel Anti-inflammatory Macrolides without Antimicrobial Activity

  摘要：

  Macrolide antibiotics, like erythromycin, clarithromycin, and azithromycin, possess anti-inflammatory properties. These properties are considered fundamental to the efficacy of these three macrolides in the treatment of chronic inflammatory diseases like diffuse panbronchiolitis and cystic fibrosis. However, long-term treatment with macrolide antibiotics presents a considerable risk for promotion of bacterial resistance. We have examined antibacterial and anti-inflammatory effects of a novel macrolide class: N'-substituted 2'-O,3'-N-carbonimidoyl bridged erythromycin-derived 14- and 15-membered macrolides. A small focused library was prepared, and compounds without antimicrobial activity, which inhibited IL-6 production, were selected. Data analysis led to a statistical model that could be used for the design of novel anti-inflammatory macrolides. The most promising compound from this library retained the anti-inflammatory activity observed with azithromycin in lipopolysaccharide-induced pulmonary neutrophilia in vivo. Importantly, this study strongly suggests that antimicrobial and anti-inflammatory activities of macrolides are independent and can be separated, which raises development plausibility of novel anti-inflammatory therapeutics.

  DOI：

  10.1021/jm300356u