N-(2-pyrrolidin-1-ylethyl)-3,5-bis(trifluoromethyl)benzamide | 1415400-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-pyrrolidin-1-ylethyl)-3,5-bis(trifluoromethyl)benzamide
• CAS: 1415400-69-9
• 化学式: C₁₅H₁₆F₆N₂O
• 分子量: 354.295
• InChiKey: RXNGEGDWNVOJKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(2-氨乙基)吡咯烷 、 3,5-双三氟甲基苯甲酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以90%的产率得到N-(2-pyrrolidin-1-ylethyl)-3,5-bis(trifluoromethyl)benzamide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of novel inhibitors against H5N1 hemagglutinin-mediated membrane fusion

  摘要：

  We reported previously that a small molecule named CL-385319 could inhibit H5N1 influenza virus infection by targeting hemagglutinin, the envelope protein mediating virus entry. In the present study, a novel series of derivatives focused on the structural variation of CL-385319 were synthesized as specific inhibitors against the H5 subtype of influenza A viruses. These small molecules inhibited the low pH-induced conformational change of hemagglutinin, thereby blocking viral entry into host cells. Compound 11 was the most active inhibitor in this series with an IC50 of 0.22 mu M. The structure activity relationships analysis of these compounds showed that the 3-fluoro-5-(trifluoromethyl)benzamide moiety was very important for activity, and the -F group was a better substituent group than -CF3 group in the phenyl ring. The inhibitory activity was sensitive to the benzamide because the oxygen and hydrogen of the amide served as H-bond acceptor and donor, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.041

文献信息

• Design, synthesis and structure–activity relationship of novel inhibitors against H5N1 hemagglutinin-mediated membrane fusion
  作者：Zhibo Zhu、Runming Li、Gaokeng Xiao、Zhipeng Chen、Jie Yang、Qiuhua Zhu、Shuwen Liu

  DOI：10.1016/j.ejmech.2012.08.041

  日期：2012.11

  We reported previously that a small molecule named CL-385319 could inhibit H5N1 influenza virus infection by targeting hemagglutinin, the envelope protein mediating virus entry. In the present study, a novel series of derivatives focused on the structural variation of CL-385319 were synthesized as specific inhibitors against the H5 subtype of influenza A viruses. These small molecules inhibited the low pH-induced conformational change of hemagglutinin, thereby blocking viral entry into host cells. Compound 11 was the most active inhibitor in this series with an IC50 of 0.22 mu M. The structure activity relationships analysis of these compounds showed that the 3-fluoro-5-(trifluoromethyl)benzamide moiety was very important for activity, and the -F group was a better substituent group than -CF3 group in the phenyl ring. The inhibitory activity was sensitive to the benzamide because the oxygen and hydrogen of the amide served as H-bond acceptor and donor, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.