(2R,3R,4S)-3-acetamido-2-((1S,2R)-2-((2-ethylhexanoyl)oxy)-3-hydroxy-1-methoxypropyl)-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid | 1169517-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,3R,4S)-3-acetamido-2-((1S,2R)-2-((2-ethylhexanoyl)oxy)-3-hydroxy-1-methoxypropyl)-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 1169517-01-4
• 化学式: C₂₁H₃₆N₄O₈
• 分子量: 472.539
• InChiKey: MGRXTHLAPGRPQZ-LYEFRCQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  33.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  193.29
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  diphenylmethyl 5-acetamido-4-(N,N'-bis-t-butoxycarbonylguanidino)-2,3,4,5,7-pentadeoxy-7-methoxy-D-glycero-D-galacto-non-2-enopyranosoate 、 2-乙基己酰氯 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-3-(2-ethylhexanoyloxy)-2-hydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid 、 (2R,3R,4S)-3-acetamido-2-((1S,2R)-2-((2-ethylhexanoyl)oxy)-3-hydroxy-1-methoxypropyl)-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vivo influenza virus-inhibitory effect of ester prodrug of 4-guanidino-7-O-methyl-Neu5Ac2en

  摘要：

  A series of ester prodrugs of 7-O-methyl derivative of Zanamivir (compound 3) was synthesized and their efficacy was evaluated in an influenza infected mice model by intranasal administration. Compound 7c (CS-8958), octanoyl ester prodrug of the C-9 alcohol of compound 3, was found to be much longer-acting than Zanamivir. Furthermore, the in vivo efficacies of compounds 12a, 12b, and 12c, the linear alkyl ester prodrug of the carboxylic acid, were comparable to that exerted by compound 7c. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.04.067