5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A | 561327-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A
• CAS: 561327-42-2
• 化学式: C₃₆H₅₈N₂O₁₁
• 分子量: 694.863
• InChiKey: DWNFFRSFQJGSML-NPTHNUJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  49.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  185.18
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以34%的产率得到(9S)-5-O-desosaminyl-9-dihydro-3-O-(3-pyridyl)acetylerythronolide A
  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 盐酸 、 甲醇 、 三甲基乙酰氯 、 三乙胺 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 5-O-desosaminyl-3-O-(3-pyridyl)acetylerythronolide A
  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