(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10-(acetoxyimino)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-4-yl 2-(pyridin-3-yl)acetate | 561327-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10-(acetoxyimino)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-4-yl 2-(pyridin-3-yl)acetate
• CAS: 561327-15-9
• 化学式: C₄₀H₆₃N₃O₁₃
• 分子量: 793.953
• InChiKey: PQRCGRVSQATAMB-HQNPHOFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  56.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  212.84
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10-(acetoxyimino)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-4-yl 2-(pyridin-3-yl)acetate 在 吡啶 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (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
• 作为产物：
  描述：

  3-O-去克拉定糖红霉素肟 在 三甲基乙酰氯 、 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10-(acetoxyimino)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-4-yl 2-(pyridin-3-yl)acetate
  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