2-[(cyclohexylacetyl)amino]-N-pyridin-2-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide | 1512843-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七噻吩
• 英文名称: 2-[(cyclohexylacetyl)amino]-N-pyridin-2-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
• 英文别名: 2-[(2-cyclohexylacetyl)amino]-N-(2-pyridyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide；2-[(2-cyclohexylacetyl)amino]-N-pyridin-2-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
• CAS: 1512843-43-4
• 化学式: C₂₃H₂₉N₃O₂S
• 分子量: 411.568
• InChiKey: OSHOMZYVRODVNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氰基-N-吡啶-2-基-乙酰胺 在 吡啶 、 ammonium acetate 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 18.5h， 生成 2-[(cyclohexylacetyl)amino]-N-pyridin-2-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
  参考文献：
  名称：

  Structural Investigation of Cycloheptathiophene-3-carboxamide Derivatives Targeting Influenza Virus Polymerase Assembly

  摘要：

  The limited number of drug classes licensed for treatment of influenza virus (Flu), together with the continuous emergence of viral variants and drug resistant mutants, highlights the urgent need to find antivirals with novel mechanisms of action. In this context, the viral RNA-dependent RNA polymerase (RdRP) subunits assembly has emerged as an attractive target. Starting from a cycloheptathiophene-3-carboxamide derivative recently identified by us for its ability to disrupt the interaction between the PA and PB1 subunits of RdRP, we have designed and synthesized a series of analogues. Their biological evaluation led to the identification of more potent protein protein interaction inhibitors, endowed with antiviral activity that also encompassed a number of clinical isolates of FluA, including an oseltamivir-resistant strain, and FluB, without showing appreciable toxicity. From this study, the cycloheptathiophene-3-carboxamide scaffold emerged as being particularly suitable to impart anti-Flu activity.

  DOI：

  10.1021/jm401560v

文献信息

• Structural Investigation of Cycloheptathiophene-3-carboxamide Derivatives Targeting Influenza Virus Polymerase Assembly
  作者：Serena Massari、Giulio Nannetti、Laura Goracci、Luca Sancineto、Giulia Muratore、Stefano Sabatini、Giuseppe Manfroni、Beatrice Mercorelli、Violetta Cecchetti、Marzia Facchini、Giorgio Palù、Gabriele Cruciani、Arianna Loregian、Oriana Tabarrini

  DOI：10.1021/jm401560v

  日期：2013.12.27

  The limited number of drug classes licensed for treatment of influenza virus (Flu), together with the continuous emergence of viral variants and drug resistant mutants, highlights the urgent need to find antivirals with novel mechanisms of action. In this context, the viral RNA-dependent RNA polymerase (RdRP) subunits assembly has emerged as an attractive target. Starting from a cycloheptathiophene-3-carboxamide derivative recently identified by us for its ability to disrupt the interaction between the PA and PB1 subunits of RdRP, we have designed and synthesized a series of analogues. Their biological evaluation led to the identification of more potent protein protein interaction inhibitors, endowed with antiviral activity that also encompassed a number of clinical isolates of FluA, including an oseltamivir-resistant strain, and FluB, without showing appreciable toxicity. From this study, the cycloheptathiophene-3-carboxamide scaffold emerged as being particularly suitable to impart anti-Flu activity.