5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)-N''-(4-tert-butoxycarbonylaminobutyl)guanidino]-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester | 1236306-99-2

• 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: 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)-N''-(4-tert-butoxycarbonylaminobutyl)guanidino]-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester
• CAS: 1236306-99-2
• 化学式: C₃₃H₅₃N₅O₁₄
• 分子量: 743.809
• InChiKey: NYUDXXKLOSBGJR-QZAJBKBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  52.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  244.58
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)-N''-(4-tert-butoxycarbonylaminobutyl)guanidino]-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses

  摘要：

  Unlike the group-2 neuraminidase, the group-1 neuraminidase of influenza virus possesses a flexible loop (the 150-loop) and a cavity (the 150-cavity) adjacent to the active site, and renders a conformational change from the 'open' form to the 'closed' form on binding with substrate (sialo-glycoprotein) or inhibitor (e.g., zanamivir). Zanamivir derivative 8a having an extended (piperazinocarbonyl)propyl substituent at the internal N-position of the guanidino group is designed as a possible inhibitor on the basis of computer docking to the open form of N1 subtype neuraminidase. Indeed, compound 8a exhibits strong neuraminidase inhibition and good anti-influenza activity against H1N1 virus with IC(50) = 2.15 mu M and EC(50) = 0.77 mu M, respectively. This study may provide a clue to future design of better group-1 neuraminidase inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.010
• 作为产物：
  描述：

  5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)thiourea]-3,4,5-trideoxy-D-glycero-D-galactonon-2-enonic acid methyl ester 、 N-叔丁氧羰基-1,4-丁二胺 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)-N''-(4-tert-butoxycarbonylaminobutyl)guanidino]-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester
  参考文献：
  名称：

  Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses

  摘要：

  Unlike the group-2 neuraminidase, the group-1 neuraminidase of influenza virus possesses a flexible loop (the 150-loop) and a cavity (the 150-cavity) adjacent to the active site, and renders a conformational change from the 'open' form to the 'closed' form on binding with substrate (sialo-glycoprotein) or inhibitor (e.g., zanamivir). Zanamivir derivative 8a having an extended (piperazinocarbonyl)propyl substituent at the internal N-position of the guanidino group is designed as a possible inhibitor on the basis of computer docking to the open form of N1 subtype neuraminidase. Indeed, compound 8a exhibits strong neuraminidase inhibition and good anti-influenza activity against H1N1 virus with IC(50) = 2.15 mu M and EC(50) = 0.77 mu M, respectively. This study may provide a clue to future design of better group-1 neuraminidase inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.010