9-脱氧-9-(丙基氨基)红霉素 | 119904-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 9-脱氧-9-(丙基氨基)红霉素
• 英文名称: 9-N-(1-propyl)erythromycylamine
• 英文别名: Erythromycin, 9-deoxy-9-(propylamino)-；(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-10-(propylamino)-oxacyclotetradecan-2-one
• CAS: 119904-03-9
• 化学式: C₄₀H₇₆N₂O₁₂
• 分子量: 777.05
• InChiKey: JDBGPLZPTBGQMX-PNSWQVPASA-N

物化性质

• 沸点：
  830.4±65.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  54
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  189
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  9-脱氧-9-(丙基氨基)红霉素 、 乙醛 以 乙腈 为溶剂， 以11%的产率得到9-((4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3-ethyl-2,10-dihydroxy-7-((5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-2,6,8,10,12,15,17-heptamethyl-14-propyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
  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
• 作为产物：
  描述：

  (9S)-9-氨基-9-脱氧乙琥红霉素 、 丙醛 在 sodium phosphate buffer 、 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以56%的产率得到9-脱氧-9-(丙基氨基)红霉素
  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

• KIRST, HERBERT A.;WIND, JULIE A.;LEEDS, JAMES P.;WILLARD, KEVIN E.;DEBONO+, J. MED. CHEM., 33,(1990) N1, C. 3086-3094
  作者：KIRST, HERBERT A.、WIND, JULIE A.、LEEDS, JAMES P.、WILLARD, KEVIN E.、DEBONO+

  DOI：——

  日期：——
• 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.