5-((2-hydroxyethyl)amino)-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile | 1380692-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-((2-hydroxyethyl)amino)-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile
• 英文别名: 5-(2-Hydroxyethylamino)-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile
• CAS: 1380692-26-1
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: GJFDVAFNGITMBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-((2-hydroxyethyl)amino)-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile 在 吡啶 、 硫化氢 、 三乙胺 作用下， 反应 13.0h， 以90%的产率得到
  参考文献：
  名称：

  4-烷基-2-芳基-1,3-恶唑[5,4-d]嘧啶-7（4 H）-硫酮和6-烷基-2-芳基-1,3-恶唑[5,4-的合成d] 2-芳酰基氨基-3,3-二氯丙烯腈的嘧啶-7（6 H）-一

  摘要：

  用过量的胺，原甲酸三乙酯和硫化氢顺序处理可及的2-芳基氨基-3,3-二氯丙烯腈，得到4-取代的恶唑[5,4 - d ]嘧啶-7（4H）-硫酮。相同试剂与甲醇钠，三氟乙酸，原甲酸三乙酯和胺的顺序反应产生6-取代的恶唑[5,4 - d ]嘧啶-7（4 H）-。

  DOI：

  10.1134/s1070363212040226
• 作为产物：
  描述：

  N-(2,2-二氯-1-氰基乙烯基)-4-甲基苯甲酰胺 、 C.I.酸性橙108 以 四氢呋喃 为溶剂， 反应 12.0h， 以67%的产率得到5-((2-hydroxyethyl)amino)-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile
  参考文献：
  名称：

  4-烷基-2-芳基-1,3-恶唑[5,4-d]嘧啶-7（4 H）-硫酮和6-烷基-2-芳基-1,3-恶唑[5,4-的合成d] 2-芳酰基氨基-3,3-二氯丙烯腈的嘧啶-7（6 H）-一

  摘要：

  用过量的胺，原甲酸三乙酯和硫化氢顺序处理可及的2-芳基氨基-3,3-二氯丙烯腈，得到4-取代的恶唑[5,4 - d ]嘧啶-7（4H）-硫酮。相同试剂与甲醇钠，三氟乙酸，原甲酸三乙酯和胺的顺序反应产生6-取代的恶唑[5,4 - d ]嘧啶-7（4 H）-。

  DOI：

  10.1134/s1070363212040226

文献信息

• In vitro activity of novel derivatives of 1,3-oxazole-4-carboxylate and 1,3-oxazole-4-carbonitrile against human cytomegalovirus
  作者：Maryna V. Kachaeva、Stepan G. Pilyo、Caroll B. Hartline、Emma A. Harden、Mark N. Prichard、Victor V. Zhirnov、Volodymyr S. Brovarets

  DOI：10.1007/s00044-019-02365-x

  日期：2019.8

  Ten 5-functionalized derivatives of 1,3-oxazole-4-carboxylate and 1,3-oxazole-4-carbonitrile were synthesized and their antiviral activities against the human cytomegalovirus (HCMV) were evaluated in vitro. Bioassays showed that seven compounds exhibited considerably higher antiviral activity (EC50:<0.05M) against a normal laboratory HCMV strain (AD-169) in human foreskin fibroblast cells than Ganciclovir (EC50=0.32M), an anti-HCMV agent in clinical use. Additionally, the HCMV-resistant isolate (GDGr K-17) was tested for sensitivity to 1,3-oxazole derivatives with most antiviral potency against the strain AD169. A one of them (5-((2-hydroxyethyl)(methyl)amino)-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile) showed very high potency (EC50:<0.05; CC50: >150 mu M, and SI50=3125) towards the resistant isolate compared to standard drugs Cidofovir (EC50=0.10 mu M, CC50: >30 mu M and SI50: <4). But, in contrast to the primary assays, the antiviral activity of these compounds against both the normal strain and the resistant isolate of HCMV were considerably less than one of Cidofovir in secondary assay. These results provided evidence that derivatives of 1,3-oxazole could be useful for developing new anti-HCMV drugs.