(E)-5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A 9-oxime 11,12-cyclic carbonate | 561327-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A 9-oxime 11,12-cyclic carbonate
• CAS: 561327-18-2
• 化学式: C₃₇H₅₇N₃O₁₂
• 分子量: 735.872
• InChiKey: SITUUCHAZDDBQU-VOBWORKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  52.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  195.77
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (E)-5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A 9-oxime 11,12-cyclic carbonate 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以20%的产率得到5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A 11,12-cyclic carbonate
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of a Novel Series of Acylides:  3-O-(3-Pyridyl)acetylerythromycin A Derivatives

  摘要：

  A novel series of acylides, 3-O-(aryl)acetylerythromycin A derivatives, were synthesized and evaluated. These compounds have significant potent antibacterial activity against not only Gram-positive pathogens, including inducibly macrolide-lincosamide-streptogramin B (MLSB)-resistant and efflux-resistant strains, but also Gram-negative pathogens, such as H. influenzae. 6,9:11,12-Dicarbonate acylide 47 (FMA0122) was twice as active against H. influenzae than azithromycin, whereas it showed only moderate in vivo efficacy in mouse protection tests. However, the 11,12-carbamate acylide 19 (TEA0929), which showed potent antibacterial activity against almost all of the main causative pathogens of community-acquired pneumonia tested, exhibited excellent in vivo efficacy comparable to those of second-generation macrolides.

  DOI：

  10.1021/jm020568d
• 作为产物：
  描述：

  在 甲醇 作用下， 以4.87 g的产率得到(E)-5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A 9-oxime 11,12-cyclic carbonate
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of a Novel Series of Acylides:  3-O-(3-Pyridyl)acetylerythromycin A Derivatives

  摘要：

  A novel series of acylides, 3-O-(aryl)acetylerythromycin A derivatives, were synthesized and evaluated. These compounds have significant potent antibacterial activity against not only Gram-positive pathogens, including inducibly macrolide-lincosamide-streptogramin B (MLSB)-resistant and efflux-resistant strains, but also Gram-negative pathogens, such as H. influenzae. 6,9:11,12-Dicarbonate acylide 47 (FMA0122) was twice as active against H. influenzae than azithromycin, whereas it showed only moderate in vivo efficacy in mouse protection tests. However, the 11,12-carbamate acylide 19 (TEA0929), which showed potent antibacterial activity against almost all of the main causative pathogens of community-acquired pneumonia tested, exhibited excellent in vivo efficacy comparable to those of second-generation macrolides.

  DOI：

  10.1021/jm020568d