(4S,5R,6R,1'S,2'R)-5-acetylamino-4-azido-6-(2',3'-diacetoxy-1'-n-tetradecyloxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 474801-56-4

• 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,1'S,2'R)-5-acetylamino-4-azido-6-(2',3'-diacetoxy-1'-n-tetradecyloxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-azido-2-[(1S,2R)-2,3-diacetyloxy-1-tetradecoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 474801-56-4
• 化学式: C₃₀H₅₀N₄O₉
• 分子量: 610.748
• InChiKey: AYBULWLPYMUNSD-RXINHCNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  43
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R,1'S,2'R)-5-acetylamino-4-azido-6-(2',3'-diacetoxy-1'-n-tetradecyloxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 Lindlar catalyst sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 (4S,5R,6R)-5-Acetylamino-6-((1R,2R)-2,3-dihydroxy-1-tetradecyloxy-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
• 作为产物：
  描述：

  methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetradecoxymethyl]-2-methoxyoxane-2-carboxylate 在 sodium azide 、 Dowex 50W (H+) 、 硫酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (4S,5R,6R,1'S,2'R)-5-acetylamino-4-azido-6-(2',3'-diacetoxy-1'-n-tetradecyloxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  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

文献信息

• Synthesis and Anti-influenza Evaluation of Polyvalent Sialidase Inhibitors Bearing 4-Guanidino-Neu5Ac2en Derivatives
  作者：Takeshi Masuda、Shuku Yoshida、Masami Arai、Satoru Kaneko、Makoto Yamashita、Takeshi Honda

  DOI：10.1248/cpb.51.1386

  日期：——

  exhibited equipotent inhibitory activity against not only influenza A virus sialidase but also influenza A virus in the cell culture. Next, we synthesized poly-L-glutamine bearing 7-O-alkyl-4-guanidino-Neu5Ac2en derivatives linked by amide bonds, 26, which showed enhanced antiviral activity against influenza A virus and more potent efficacy in vivo relative to a monomeric sialidase inhibitor.

  描述了在聚-L-谷氨酰胺主链上带有4-胍基-Neu5Ac2en衍生物的多价唾液酸酶抑制剂。为了更长的4-胍基-Neu5Ac2en（扎那米韦）在支气管和肺中的保留时间，我们集中研究了带有4-胍基-Neu5Ac2en衍生物通过不可裂解的烷基醚键键合在其C-7位的超分子。我们首先发现唾液酸衍生物8的7-羟基的烷基化进展顺利，并产生了7-O-烷基-4-胍基-Neu5Ac2en衍生物13，其不仅对甲型流感病毒唾液酸酶而且对流感都表现出同等的抑制活性。细胞培养物中的病毒。接下来，我们合成了带有通过酰胺键连接的7-O-烷基-4-胍基-Neu5Ac2en衍生物的聚L-谷氨酰胺26，