(4S,5R,6R)-4-azido-5-(2-oxo-pyrrolidin-1-yl)-6-(1R,2R,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 176507-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,5R,6R)-4-azido-5-(2-oxo-pyrrolidin-1-yl)-6-(1R,2R,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4S)-4-azido-3-(2-oxopyrrolidin-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 176507-85-0
• 化学式: C₁₄H₂₀N₄O₇
• 分子量: 356.335
• InChiKey: FDIXYBYKICHIDY-RFCPQYNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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)-4-azido-5-(2-oxo-pyrrolidin-1-yl)-6-(1R,2R,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 179.0h， 生成 (4S,5R,6R)-4-amino-5-(2-oxo-pyrrolidin-1-yl)-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
• 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 、 盐酸 、 4-二甲氨基吡啶 、 sodium methylate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 203.17h， 生成 (4S,5R,6R)-4-azido-5-(2-oxo-pyrrolidin-1-yl)-6-(1R,2R,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.