(4S,5R,6R)-5-(Acetyl-methyl-amino)-4-azido-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 176507-88-3

• 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)-5-(Acetyl-methyl-amino)-4-azido-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4S)-3-[acetyl(methyl)amino]-4-azido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 176507-88-3
• 化学式: C₁₃H₂₀N₄O₇
• 分子量: 344.324
• InChiKey: JUKYAUNNKCZHJT-RULNCXCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-5-(Acetyl-methyl-amino)-4-azido-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.0h， 生成 (4S,5R,6R)-5-(acetyl-methyl-amino)-4-amino-6-(1R,2R,3-hydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents

  摘要：

  Analogues of 4-guanidino-Neu5Ac2en (GG167) have been prepared containing alternative amide and sulfonamide substituents at the 5-position. (4S,5R,6R)-4-guanidino-5-(2,2,2-trifluoroacetylamino)-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 5 and (4S,5R,6R)-4-guanidino-5-methanesulfonylamino-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 6 were the only analogues which approached the activity of GG167, showing potent inhibition of influenza virus sialidases and good antiviral activity in vitro.

  DOI：

  10.1016/0223-5234(96)80447-8
• 作为产物：
  描述：

  甲基(3aR,4R,7aR)-2-甲基-4-[(1S,2R)-1,2,3-三乙酰氧基丙基]-3a,7a-二氢-4H-吡喃并[3,4-d][1,3]恶唑-6-羧酸酯 在 吡啶 、 sodium azide 、 sodium methylate 、 四丁基硫酸氢铵 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 (4S,5R,6R)-5-(Acetyl-methyl-amino)-4-azido-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents

  摘要：

  Analogues of 4-guanidino-Neu5Ac2en (GG167) have been prepared containing alternative amide and sulfonamide substituents at the 5-position. (4S,5R,6R)-4-guanidino-5-(2,2,2-trifluoroacetylamino)-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 5 and (4S,5R,6R)-4-guanidino-5-methanesulfonylamino-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 6 were the only analogues which approached the activity of GG167, showing potent inhibition of influenza virus sialidases and good antiviral activity in vitro.

  DOI：

  10.1016/0223-5234(96)80447-8

文献信息

• Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents
  作者：PW Smith、ID Starkey、PD Howes、SL Sollis、SP Keeling、PC Cherry、M von Itzstein、WY Wu、B Jin

  DOI：10.1016/0223-5234(96)80447-8

  日期：1996.1

  Analogues of 4-guanidino-Neu5Ac2en (GG167) have been prepared containing alternative amide and sulfonamide substituents at the 5-position. (4S,5R,6R)-4-guanidino-5-(2,2,2-trifluoroacetylamino)-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 5 and (4S,5R,6R)-4-guanidino-5-methanesulfonylamino-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 6 were the only analogues which approached the activity of GG167, showing potent inhibition of influenza virus sialidases and good antiviral activity in vitro.