N’-(3-(4-(tert-butyl)phenyl)acryloyl)-4-methylbenzohydrazide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N’-(3-(4-(tert-butyl)phenyl)acryloyl)-4-methylbenzohydrazide
• 英文别名: N'-[(E)-3-(4-tert-butylphenyl)prop-2-enoyl]-4-methylbenzohydrazide
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: AYKLKZBEGGGKGH-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲基苯甲酸乙酯 在 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 N’-(3-(4-(tert-butyl)phenyl)acryloyl)-4-methylbenzohydrazide
  参考文献：
  名称：

  Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus

  摘要：

  Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.054

文献信息

• Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus
  作者：Gilda Giancotti、Michela Cancellieri、Andrea Balboni、Mariateresa Giustiniano、Ettore Novellino、Leen Delang、Johan Neyts、Pieter Leyssen、Andrea Brancale、Marcella Bassetto

  DOI：10.1016/j.ejmech.2018.02.054

  日期：2018.4

  Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus. (C) 2018 Elsevier Masson SAS. All rights reserved.