tert-butyl (2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate | 1375881-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl (2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate
• CAS: 1375881-21-2
• 化学式: C₁₈H₂₂N₆O₂
• 分子量: 354.412
• InChiKey: VMZMCWWYMUZYIN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  106.98
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 15.0h， 生成 methyl N-[(2S)-1-[(2S)-2-[4-(4-azidophenyl)-5-bromo-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and evaluation of non-dimeric HCV NS5A inhibitors

  摘要：

  Based on the symmetrical bidentate structure of the NS5A inhibitor BMS-790052, a series of new monodentate molecules were designed. The synthesis of 36 new non-dimeric NS5A inhibitors is reported along with their ability to block HCV replication in an HCV 1b replicon system. Among them compound 5a showed picomolar range activity along with an excellent selectivity index (SI > 90,000). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.023
• 作为产物：
  描述：

  2-O-[2-(4-azidophenyl)-2-oxoethyl] 1-O-tert-butyl (2S)-pyrrolidine-1,2-dicarboxylate 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 生成 tert-butyl (2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of non-dimeric HCV NS5A inhibitors

  摘要：

  Based on the symmetrical bidentate structure of the NS5A inhibitor BMS-790052, a series of new monodentate molecules were designed. The synthesis of 36 new non-dimeric NS5A inhibitors is reported along with their ability to block HCV replication in an HCV 1b replicon system. Among them compound 5a showed picomolar range activity along with an excellent selectivity index (SI > 90,000). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.023

文献信息

• Synthesis and biological evaluation of new potent and selective HCV NS5A inhibitors
  作者：Junxing Shi、Longhu Zhou、Franck Amblard、Drew R. Bobeck、Hongwang Zhang、Peng Liu、Lavanya Bondada、Tamara R. McBrayer、Phillip M. Tharnish、Tony Whitaker、Steven J. Coats、Raymond F. Schinazi

  DOI：10.1016/j.bmcl.2012.03.089

  日期：2012.5

  NS5A inhibitors are a new class of direct-acting antiviral agents which display very potent anti-HCV activity in vitro and in humans. Rationally designed modifications to the central biphenyl linkage of a known NS5A series led to selection of several compounds that were synthesized and evaluated in a HCV genotype 1b replicon. The straight triphenyl linked compound 11a showed similar anti-HCV activity to the clinical compound BMS-790052 and a superior cytotoxicity profile in three different cell lines, with an EC50 value of 26 pM and a therapeutic index of over four million in an HCV replicon assay. This triphenyl analog warrants further preclinical evaluation as an anti-HCV agent. (C) 2012 Published by Elsevier Ltd.