methyl 5-acetamido-4,8,9-tri-O-acetyl-2,3,5-trideoxy-7-O-ethyl-D-glycero-D-galacto-non-2-enopyranosoate | 203120-27-8

• 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: methyl 5-acetamido-4,8,9-tri-O-acetyl-2,3,5-trideoxy-7-O-ethyl-D-glycero-D-galacto-non-2-enopyranosoate
• CAS: 203120-27-8
• 化学式: C₂₀H₂₉NO₁₁
• 分子量: 459.45
• InChiKey: PLDYQDXFPAYCKS-AIHBUXEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-4,8,9-tri-O-acetyl-2,3,5-trideoxy-7-O-ethyl-D-glycero-D-galacto-non-2-enopyranosoate 在 甲醇 、 三氟化硼乙醚 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 以63%的产率得到(4S,5R,6R,1'S,2'R)-5-acetylamino-4-azido-6-(2',3'-diacetoxy-1'-ethoxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Neuraminic acid derivatives, their preparation and their medical use

  摘要：

  化合物的结构式(I)或其盐或酯：具有出色的唾液酸酶抑制活性，因此可用于治疗和预防流感和其他病毒性疾病，其中病毒的复制易受唾液酸酶抑制剂的影响。

  公开号：

  US06340702B1
• 作为产物：
  描述：

  (3S,4R,5S,6R)-3-Amino-5-ethoxy-6-hydroxymethyl-tetrahydro-pyran-2,4-diol 在 N-acetylneuraminic acid aldolase 、 Dowex 50W (H+) 、 硫酸 、 sodium acetate 、 溶剂黄146 作用下， 生成 methyl 5-acetamido-4,8,9-tri-O-acetyl-2,3,5-trideoxy-7-O-ethyl-D-glycero-D-galacto-non-2-enopyranosoate
  参考文献：
  名称：

  Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives

  摘要：

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00328-1

文献信息

• Synthesis and anti-Influenza virus activity of 7-O-Alkylated derivatives related to zanamivir
  作者：Takeshi Honda、Takeshi Masuda、Shuku Yoshida、Masami Arai、Satoru Kaneko、Makoto Yamashita

  DOI：10.1016/s0960-894x(02)00329-3

  日期：2002.8

  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.