1-Benzyl-2-[4-(benzyloxy)phenyl]-4-oxoazetidine-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-Benzyl-2-[4-(benzyloxy)phenyl]-4-oxoazetidine-2-carbonitrile
• 英文别名: 1-benzyl-4-oxo-2-(4-phenylmethoxyphenyl)azetidine-2-carbonitrile
• 化学式: C₂₄H₂₀N₂O₂
• 分子量: 368.435
• InChiKey: MOWCTZRQNKKJKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(benzylamino)-2-(4-phenylmethoxyphenyl)acetonitrile 在 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 7.0h， 生成 1-Benzyl-2-[4-(benzyloxy)phenyl]-4-oxoazetidine-2-carbonitrile
  参考文献：
  名称：

  Anti-human immunodeficiency activity of novel 2-arylpyrrolidine analogs

  摘要：

  A series of 26 new compounds were synthesized and screened for their anti-human immunodeficiency virus-1 and cytotoxicity activity. Of these, 14 were found to be inhibitors of human immunodeficiency virus replications in primary human lymphocytes with 50 % effective concentration values < 20 A mu M. Moreover, most of the compounds were cytotoxic to human lymphocytes, CEM, and Vero cells. Our structure activity relationship study identified different patterns. Compounds 2g-j and 4 (whose structure is closer to the loviride structure) were very potent. Comparing the activity of the compounds containing the 2-aryl substituents, we observed that compounds with benzyloxyphenyl groups were more potent. Compounds in which the 1-aryl moiety contained methyl group in 4- or 3,5-positions also showed high activity. In the series of compounds containing the nitrile, amine, and amide groups, we observed a decrease in activity with CN > NH2 > C(O)NH2. The difference of activity between the 5-membered and 4-membered rings compounds was not significant. This initial information could be used to design improved anti-human immunodeficiency virus compounds in this class.

  DOI：

  10.1007/s00044-016-1731-7

文献信息

• Anti-human immunodeficiency activity of novel 2-arylpyrrolidine analogs
  作者：Ashot H. Martirosyan、Sahak P. Gasparyan、Marina V. Alexanyan、Gohar K. Harutyunyan、Henry A. Panosyan、Raymond F. Schinazi

  DOI：10.1007/s00044-016-1731-7

  日期：2017.1

  A series of 26 new compounds were synthesized and screened for their anti-human immunodeficiency virus-1 and cytotoxicity activity. Of these, 14 were found to be inhibitors of human immunodeficiency virus replications in primary human lymphocytes with 50 % effective concentration values < 20 A mu M. Moreover, most of the compounds were cytotoxic to human lymphocytes, CEM, and Vero cells. Our structure activity relationship study identified different patterns. Compounds 2g-j and 4 (whose structure is closer to the loviride structure) were very potent. Comparing the activity of the compounds containing the 2-aryl substituents, we observed that compounds with benzyloxyphenyl groups were more potent. Compounds in which the 1-aryl moiety contained methyl group in 4- or 3,5-positions also showed high activity. In the series of compounds containing the nitrile, amine, and amide groups, we observed a decrease in activity with CN > NH2 > C(O)NH2. The difference of activity between the 5-membered and 4-membered rings compounds was not significant. This initial information could be used to design improved anti-human immunodeficiency virus compounds in this class.