3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((phenyl)methyl)azetidin-3-yl)imino)erythromycin A | 893556-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((phenyl)methyl)azetidin-3-yl)imino)erythromycin A
• 英文别名: (1S,2R,5R,7R,8R,9R,11R,13R,14R)-15-(1-benzylazetidin-3-yl)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
• CAS: 893556-39-3
• 化学式: C₄₁H₆₃N₃O₁₀
• 分子量: 757.965
• InChiKey: CDHZUHPVNFOXOM-NDXFOWBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  54
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(azetidin-3-yl)-imino)-erythromycin A dihydrochloride 、 苯甲醛 在 溶剂黄146 、 三乙胺 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以47%的产率得到3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((phenyl)methyl)azetidin-3-yl)imino)erythromycin A
  参考文献：
  名称：

  Discovery of Azetidinyl Ketolides for the Treatment of Susceptible and Multidrug Resistant Community-Acquired Respiratory Tract Infections

  摘要：

  Respiratory tract bacterial strains are becoming increasingly resistant to currently marketed macrolide antibiotics. The current alternative telithromycin (1) from the newer ketolide class of macrolides addresses resistance but is hampered by serious safety concerns, hepatotoxicity in particular. We have discovered a novel series of azetidinyl ketolides that focus on mitigation of hepatotoxicity by minimizing hepatic turnover and time-dependent inactivation of CYP3A isoforms in the liver without compromising the potency and efficacy of 1.

  DOI：

  10.1021/jm900729s