9-N-(1-propyl)-9-N,11-O-methyleneerythromycylamine | 112452-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-N-(1-propyl)-9-N,11-O-methyleneerythromycylamine
• 英文别名: (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,17S)-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-14-propyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
• CAS: 112452-24-1
• 化学式: C₄₁H₇₆N₂O₁₂
• 分子量: 789.061
• InChiKey: GZXCXGYLXDXFCM-IVOAIFJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  55
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.98
• 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：

  (9S)-9-氨基-9-脱氧乙琥红霉素 在 sodium phosphate buffer 、 sodium cyanoborohydride 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 生成 9-N-(1-propyl)-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.