(4S,5R,6R)-5-amino-4-guanidino-6-(1R,2R,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid | 171887-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R,6R)-5-amino-4-guanidino-6-(1R,2R,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
• 英文别名: (2R,3R,4S)-3-amino-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 171887-00-6
• 化学式: C₁₀H₁₈N₄O₆
• 分子量: 290.276
• InChiKey: WRSQKOMSGSJKGQ-LRGKAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  198
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三氟乙酸甲酯 、 (4S,5R,6R)-5-amino-4-guanidino-6-(1R,2R,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 在 三乙胺 作用下， 反应 72.0h， 以30%的产率得到(4S,5R,6R)-4-guanidino-5-(2,2,2-trifluoro-acetylamino)-6-(1R,2R,3-trihydroxypropyl)-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：

  5-乙酰氨基-7,8,9-O-三乙酰基-2,6-脱水-4-叠氮-3,4,5-三脱氧-D-甘油-D-半乳-2-壬烯酸甲酯 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium methylate 、 potassium carbonate 、 三苯基膦 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 117.0h， 生成 (4S,5R,6R)-5-amino-4-guanidino-6-(1R,2R,3-trihydroxy-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

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.