(4S,5R,6R)-5-Acetylamino-6-[(1R,2R)-1-(2-acetylamino-ethoxy)-2,3-dihydroxy-propyl]-4-guanidino-5,6-dihydro-4H-pyran-2-carboxylic acid; compound with trifluoro-acetic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R,6R)-5-Acetylamino-6-[(1R,2R)-1-(2-acetylamino-ethoxy)-2,3-dihydroxy-propyl]-4-guanidino-5,6-dihydro-4H-pyran-2-carboxylic acid; compound with trifluoro-acetic acid
• 英文别名: (2R,3R,4S)-3-acetamido-2-[(1R,2R)-1-(2-acetamidoethoxy)-2,3-dihydroxypropyl]-4-(diaminomethylideneamino)-3,4-dihydro-2H-pyran-6-carboxylic acid;2,2,2-trifluoroacetic acid
• 化学式: C₂HF₃O₂*C₁₆H₂₇N₅O₈
• 分子量: 531.443
• InChiKey: DAACYRWULUBIHO-QZDHACKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.78
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  256
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  (4S,5R,6R,1'S,4''R)-5-acetylamino-4-(bis-N,N'-tert-butyloxycarbonyl)guanidino-6-[(2'''-azidoethyloxy)-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)]methyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 Lindlar catalyst 吡啶 、 sodium hydroxide 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (4S,5R,6R)-5-Acetylamino-6-[(1R,2R)-1-(2-acetylamino-ethoxy)-2,3-dihydroxy-propyl]-4-guanidino-5,6-dihydro-4H-pyran-2-carboxylic acid; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis and anti-Influenza virus activity of 7-O-Alkylated derivatives related to zanamivir

  摘要：

  A series of 7-alkyl ether derivatives related to zanamivir were synthesized using direct alkylation of the C-7 alcohol of sialic acid. Alkyl ether moiety of less than 12 carbons in length showed low nanomolar inhibitory activity against influenza A virus sialidase. Furthermore, their moiety improved influenza A virus plaque reduction activity compared to zanamivir. However, removal of the 8,9-diol of the 7-O-alkyl derivatives resulted in loss of antiviral potency. This result suggests that 8,9-diol must play an important role in binding with both influenza A and B virus sialidases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00329-3