methyl (2S,4S)-4-amino-1-((tert-butoxycarbonyl)-L-isoleucyl)pyrrolidine-2-carboxylate | 934552-76-8

• 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: methyl (2S,4S)-4-amino-1-((tert-butoxycarbonyl)-L-isoleucyl)pyrrolidine-2-carboxylate
• CAS: 934552-76-8
• 化学式: C₁₇H₃₁N₃O₅
• 分子量: 357.45
• InChiKey: NKDYJONULSWEQG-CYDGBPFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  110.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S)-4-amino-1-((tert-butoxycarbonyl)-L-isoleucyl)pyrrolidine-2-carboxylate 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 以63.4%的产率得到tert-butyl 1-[4-amino-2-(hydroxycarbamoyl)pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-ylcarbamate
  参考文献：
  名称：

  Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors

  摘要：

  A series of pyrrolidine derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially 4-hydroXy-L-proline using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A neuraminidase. Within this series, five compounds, 6e, 9c, 9e, 9f, and 10e, have good potency (IC50 = 1.56-2.71 mu M) which are compared to that the NA inhibitor Oseltarnivir (IC50 = 1.06 mu M), and could be used as lead compoundS in the future. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.020
• 作为产物：
  描述：

  N^α-Boc-Ile-OBt 在 Lindlar's catalyst N-甲基吗啉 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 55.0 ℃ 、101.33 kPa 条件下， 反应 24.75h， 生成 methyl (2S,4S)-4-amino-1-((tert-butoxycarbonyl)-L-isoleucyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors

  摘要：

  A series of pyrrolidine derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially 4-hydroXy-L-proline using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A neuraminidase. Within this series, five compounds, 6e, 9c, 9e, 9f, and 10e, have good potency (IC50 = 1.56-2.71 mu M) which are compared to that the NA inhibitor Oseltarnivir (IC50 = 1.06 mu M), and could be used as lead compoundS in the future. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.020