9-N-(3-cyano-1-propyl)erythromycylamine | 112459-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-N-(3-cyano-1-propyl)erythromycylamine
• 英文别名: 4-[[(2R,3S,4R,5S,6S,7R,9R,10R,11S,12S,13R)-10-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,9-trihydroxy-12-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]amino]butanenitrile
• CAS: 112459-33-3
• 化学式: C₄₁H₇₅N₃O₁₂
• 分子量: 802.059
• InChiKey: OIPNNSZBMSPXBC-PHNQTDPPSA-N

物化性质

• 熔点：
  135-140 °C
• 沸点：
  881.1±65.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  56
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  213
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  9-N-(3-cyano-1-propyl)erythromycylamine 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、413.68 kPa 条件下， 以20%的产率得到9-N-(4-amino-1-butyl)erythromycylamine
  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：

  4-氧代丁腈 、 (9S)-9-氨基-9-脱氧乙琥红霉素 在 盐酸 、 sodium phosphate buffer 、 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以19%的产率得到9-N-(3-cyano-1-propyl)erythromycylamine
  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：——