(4S,5R,6R)-5-Acetylamino-4-guanidino-6-propylcarbamoyl-5,6-dihydro-4H-pyran-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (4S,5R,6R)-5-Acetylamino-4-guanidino-6-propylcarbamoyl-5,6-dihydro-4H-pyran-2-carboxylic acid
• 英文别名: (2R,3R,4S)-3-acetamido-4-guanidino-2-(propylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylic acid；(2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-(propylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylic acid
• 化学式: C₁₃H₂₁N₅O₅
• 分子量: 327.34
• InChiKey: IZQHJLQEZZNCJI-FXBDTBDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (tert-butoxycarbonylamino)pyrazol-1-yl-methyl carbamic acid tert-butyl ester 、 (4S,5R,6R)-5-Acetylamino-4-amino-6-propylcarbamoyl-5,6-dihydro-4H-pyran-2-carboxylic acid benzhydryl ester 在 三乙胺 、 三氟乙酸 作用下， 生成 (4S,5R,6R)-5-Acetylamino-4-guanidino-6-propylcarbamoyl-5,6-dihydro-4H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Novel inhibitors of influenza sialidase related to GG167 Synthesis of 4-amino and guanidino-4H-pyran-2-carboxylic acid-6-propylamides; selective inhibitors of influenza a virus sialidase

  摘要：

  N-Propylcarboxamides 1a,b-3a,b have been synthesised from 2,3-didehydro-2,4-dideoxy-4-amino-N-acetylneuraminic acid 4. The tertiary amides 2a,b-3a,b are highly potent but selective inhibitors of influenza A sialidase. The exceptional inhibitory activity of the dipropylamides 3a and 3b against influenza A shows that the 6-dipropylcarboxamide substituent is preferable to the polar glycerol sidechain found in the related sialidase inhibitors GG167 and 4. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00318-6

文献信息

• Novel inhibitors of influenza sialidase related to GG167 Synthesis of 4-amino and guanidino-4H-pyran-2-carboxylic acid-6-propylamides; selective inhibitors of influenza a virus sialidase
  作者：Steven L. Sollis、Paul W. Smith、Peter D. Howes、Peter C. Cherry、Richard C. Bethell

  DOI：10.1016/0960-894x(96)00318-6

  日期：1996.8

  N-Propylcarboxamides 1a,b-3a,b have been synthesised from 2,3-didehydro-2,4-dideoxy-4-amino-N-acetylneuraminic acid 4. The tertiary amides 2a,b-3a,b are highly potent but selective inhibitors of influenza A sialidase. The exceptional inhibitory activity of the dipropylamides 3a and 3b against influenza A shows that the 6-dipropylcarboxamide substituent is preferable to the polar glycerol sidechain found in the related sialidase inhibitors GG167 and 4. Copyright (C) 1996 Elsevier Science Ltd