| 1307759-57-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• CAS: 1307759-57-4
• 化学式: C₄₇H₇₃N₅O₁₃
• 分子量: 916.122
• InChiKey: QTNHWXBCLPXDKH-GIKLZMENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  65.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  214.12
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  4-(1H-吡唑-1-基)苯基异硫氰酸酯 、 3'-N-demethyl-6-O-methyl-9a-aza-9a-homoerythromycin A 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