(2R,3R,4S)-4-(diaminomethylideneamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid | 1054642-64-6

• 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: (2R,3R,4S)-4-(diaminomethylideneamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 1054642-64-6
• 化学式: C₁₅H₂₆N₄O₈
• 分子量: 390.393
• InChiKey: BWJPVVWIEFSQCI-CNYIRLTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  210
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-4-(diaminomethylideneamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid 在 三乙胺 、 三氟乙酸 作用下， 反应 74.0h， 生成 (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 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 115.0h， 生成 (2R,3R,4S)-4-(diaminomethylideneamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-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