N-(2-methyl-3-oxo-8-phenyl-1-thia-4-azaspiro[4.5]decan-4-yl)adamantane-1-carboxamide | 1415559-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: N-(2-methyl-3-oxo-8-phenyl-1-thia-4-azaspiro[4.5]decan-4-yl)adamantane-1-carboxamide
• CAS: 1415559-02-2
• 化学式: C₂₆H₃₄N₂O₂S
• 分子量: 438.634
• InChiKey: COHNHEZZNRSRPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-苯基环己酮 、 金刚烷-1-甲酰肼 、 硫代乳酸 以 甲苯 为溶剂， 反应 0.17h， 以84.01%的产率得到N-(2-methyl-3-oxo-8-phenyl-1-thia-4-azaspiro[4.5]decan-4-yl)adamantane-1-carboxamide
  参考文献：
  名称：

  Microwave assisted synthesis and anti-influenza virus activity of 1-adamantyl substituted N-(1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives

  摘要：

  A microwave-assisted three-component one-pot cyclocondensation method was applied for the synthesis of novel N-(1-thia-4-azaspiro[4.5] decan-4-yl)carboxamide compounds carrying an adamantyl moiety. The structures of the compounds were confirmed by spectral and elemental analysis. All compounds were evaluated for antiviral activity against influenza A (H1N1 and H3N2) and influenza B virus in MDCK cell cultures. The compounds displayed a confined structure-activity relationship. The N-(2,8-dimethyl-3-oxo-1-thia-4-azaspiro[4.5] dec-4-yl)adamantane-1-carboxamide 3b was the most potent inhibitor [antiviral EC50: 1.4 mu M against influenza A/H3N2 virus]. Its strong inhibitory effect in a virus hemolysis assay supports that 3b acts as an influenza virus fusion inhibitor by preventing the conformational change of the influenza virus hemagglutinin at low pH. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.064

文献信息

• Microwave assisted synthesis and anti-influenza virus activity of 1-adamantyl substituted N-(1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives
  作者：Füsun Göktaş、Evelien Vanderlinden、Lieve Naesens、Nesrin Cesur、Zafer Cesur

  DOI：10.1016/j.bmc.2012.09.064

  日期：2012.12

  A microwave-assisted three-component one-pot cyclocondensation method was applied for the synthesis of novel N-(1-thia-4-azaspiro[4.5] decan-4-yl)carboxamide compounds carrying an adamantyl moiety. The structures of the compounds were confirmed by spectral and elemental analysis. All compounds were evaluated for antiviral activity against influenza A (H1N1 and H3N2) and influenza B virus in MDCK cell cultures. The compounds displayed a confined structure-activity relationship. The N-(2,8-dimethyl-3-oxo-1-thia-4-azaspiro[4.5] dec-4-yl)adamantane-1-carboxamide 3b was the most potent inhibitor [antiviral EC50: 1.4 mu M against influenza A/H3N2 virus]. Its strong inhibitory effect in a virus hemolysis assay supports that 3b acts as an influenza virus fusion inhibitor by preventing the conformational change of the influenza virus hemagglutinin at low pH. (C) 2012 Elsevier Ltd. All rights reserved.