9-N-benzyl-9-N,11-O-methyleneerythromycylamine | 112452-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-N-benzyl-9-N,11-O-methyleneerythromycylamine
• 英文别名: (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,17S)-14-benzyl-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2,10-dihydroxy-7-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
• CAS: 112452-26-3
• 化学式: C₄₅H₇₆N₂O₁₂
• 分子量: 837.105
• InChiKey: IGHCLLDIKYXLRN-TWXYIZTISA-N

物化性质

• 沸点：
  878.2±65.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  59
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 9-N-benzylerythromycylamine 以 水 、 乙腈 为溶剂， 反应 4.25h， 以22%的产率得到9-N-benzyl-9-N,11-O-methyleneerythromycylamine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of new 9-N-alkyl derivatives of 9(S)-erythromycylamine

  摘要：

  A series of new 9-N-alkyl derivatives of 9(S)-erythromycylamine has been synthesized by reductive alkylation of erythromycylamine with aliphatic aldehydes and sodium cyanoborohydride. Alternative syntheses employing hydrogenation methods have also been developed. These new 9-N-alkyl derivatives possess excellent antimicrobial activity in vitro and in vivo, especially when administered orally to treat experimental infections in mice. From structure-activity studies, 9-N-(1-propyl)erythromycylamine (LY281389) was selected as the most efficacious derivative. These methods have also been extended to the synthesis of some 9-N,N-dialkyl derivatives of erythromycylamine.

  DOI：

  10.1021/jm00173a028

文献信息

• Synthesis and structure-activity relationships of new 9-N-alkyl derivatives of 9(S)-erythromycylamine
  作者：Herbert A. Kirst、Julie A. Wind、James P. Leeds、Kevin E. Willard、Manuel Debono、Rosanne Bonjouklian、James M. Greene、Kevin A. Sullivan、Jonathan W. Paschal

  DOI：10.1021/jm00173a028

  日期：1990.11

  A series of new 9-N-alkyl derivatives of 9(S)-erythromycylamine has been synthesized by reductive alkylation of erythromycylamine with aliphatic aldehydes and sodium cyanoborohydride. Alternative syntheses employing hydrogenation methods have also been developed. These new 9-N-alkyl derivatives possess excellent antimicrobial activity in vitro and in vivo, especially when administered orally to treat experimental infections in mice. From structure-activity studies, 9-N-(1-propyl)erythromycylamine (LY281389) was selected as the most efficacious derivative. These methods have also been extended to the synthesis of some 9-N,N-dialkyl derivatives of erythromycylamine.