9-N-<3-(methylthio)-1-propyl>erythromycylamine | 112452-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-N-<3-(methylthio)-1-propyl>erythromycylamine
• 英文别名: 9-N-[3-(methylthio)-1-propyl]erythromycylamine；(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-(3-methylsulfanylpropylamino)-oxacyclotetradecan-2-one
• CAS: 112452-19-4
• 化学式: C₄₁H₇₈N₂O₁₂S
• 分子量: 823.143
• InChiKey: IDCALIJHBPWXFD-PHNQTDPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  56
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  214
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  3-甲硫基丙醛 、 (9S)-9-氨基-9-脱氧乙琥红霉素 在 sodium phosphate buffer 、 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以13%的产率得到9-N-<3-(methylthio)-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：——