2,5-bis(4-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)thiophene | 1375881-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,5-bis(4-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)thiophene
• CAS: 1375881-31-4
• 化学式: C₃₀H₃₀N₆S
• 分子量: 506.674
• InChiKey: VLSKVELBUOVIHP-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.42
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,5-bis(4-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)thiophene 、 MOC-L-缬氨酸 在 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 乙腈 为溶剂， 反应 14.0h， 生成 methyl N-[(2S)-1-[(2S)-2-[5-[4-[5-[4-[2-[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]thiophen-2-yl]phenyl]-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of new potent and selective HCV NS5A inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.03.089
• 作为产物：
  描述：

  (S)-2-[5-(4-溴苯基)-1H-咪唑-2-基]吡咯烷-1-羧酸叔丁酯 在 盐酸 、 四(三苯基膦)钯 、 水 、 potassium acetate 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 34.0h， 生成 2,5-bis(4-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)thiophene
  参考文献：
  名称：

  Synthesis and biological evaluation of new potent and selective HCV NS5A inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.03.089