5-acetamido-4-guanidino-2,3,4,5-tetradeoxy-7-methoxy-D-glycero-D-galacto-non-2-enopyranosoic acid trifluoroacetic acid salt | 203120-18-7

• 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-4-guanidino-2,3,4,5-tetradeoxy-7-methoxy-D-glycero-D-galacto-non-2-enopyranosoic acid trifluoroacetic acid salt
• 英文别名: 5-acetamido-4-guanidino-2,3,4,5-tetradeoxy-7-O-methyl-D-glycero-D-galacto-non-2-enopyranosoic acid trifluoroacetate；Laninamivir trifluoroacetate；(2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid;2,2,2-trifluoroacetic acid
• CAS: 203120-18-7
• 化学式: C₂HF₃O₂*C₁₃H₂₂N₄O₇
• 分子量: 460.364
• InChiKey: DAGFMLSFZMOWFA-WWIZLJSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  227
• 氢给体数：
  7
• 氢受体数：
  13

制备方法与用途

兰尼米韦三氟醋酸盐是一种抗病毒化合物，用于治疗和预防甲型和乙型流感病毒。这是一种通过鼻腔吸入给药的长效神经氨酸酶抑制剂。

反应信息

• 作为反应物：
  描述：

  5-acetamido-4-guanidino-2,3,4,5-tetradeoxy-7-methoxy-D-glycero-D-galacto-non-2-enopyranosoic acid trifluoroacetic acid salt 在 氨 作用下， 以 水 为溶剂， 生成 (4S,5R,6R)-5-乙酰氨基-4-胍基-6-((1R,2R)-2,3-二羟基-1-甲氧基丙基)-5,6-二氢-4H-吡喃-2-甲酸
  参考文献：
  名称：

  DRUG FOR TREATMENT OF INFLUENZA

  摘要：

  公开号：

  EP2123271B1
• 作为产物：
  描述：

  2-acetamido-1,6:3,4-dianhydro-2-deoxy-β-D-talopyranose 在 Lindlar catalyst 盐酸 、 sodium hydroxide 、 sodium azide 、 N-acetylneuraminic acid aldolase 、 Dowex 50W (H+) 、 硫酸 、 氢气 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-acetamido-4-guanidino-2,3,4,5-tetradeoxy-7-methoxy-D-glycero-D-galacto-non-2-enopyranosoic acid trifluoroacetic acid salt
  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

• Neuraminic acid derivatives, their preparation and their medical use
  申请人：Sankyo Company, Limited

  公开号：US06340702B1

  公开（公告）日：2002-01-22

  Compounds of formula (I) or their salts or esters: have excellent sialidase inhibitory activity and are therefore useful for the treatment and prevention of influenza and other viral diseases where the replication of the virus is susceptible to sialidase inhibitors.

  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。
• DRUG FOR TREATMENT OF INFLUENZA
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2123271B1

  公开（公告）日：2011-10-05
• Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives
  作者：Takeshi Honda、Takeshi Masuda、Shuku Yoshida、Masami Arai、Yoshiyuki Kobayashi、Makoto Yamashita

  DOI：10.1016/s0960-894x(02)00328-1

  日期：2002.8

  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.