2-(1-adamantyl)ethyl 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazole-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1-adamantyl)ethyl 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazole-3-carboxylate
• 英文别名: 2-(1-Adamantyl)ethyl 5-[hydroxy(oxolan-2-yl)amino]-1,2-oxazole-3-carboxylate；2-(1-adamantyl)ethyl 5-[hydroxy(oxolan-2-yl)amino]-1,2-oxazole-3-carboxylate
• 化学式: C₂₀H₂₈N₂O₅
• 分子量: 376.453
• InChiKey: RNHOAJFMWVCHFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(1-adamantyl)ethyl acrylate 在 盐酸 、 三乙胺 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.67h， 生成 2-(1-adamantyl)ethyl 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazole-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 5-hydroxylaminoisoxazole derivatives as lipoxygenase inhibitors and metabolism enhancing agents

  摘要：

  A versatile synthesis of novel 5-hydroxylaminoisoxazoles bearing adamantane moieties has been accomplished using the heterocyclization reactions of readily available unsaturated esters by the treatment with tetranitromethane in the presence of triethylamine and subsequent reduction of resulting 5-nitroisoxazoles by SnCl2 with the participation of THF. A number of obtained isoxazole derivatives were evaluated for their antioxidative activity, inhibition of lipoxygenases and impact on the rat liver mitochondria. The majority of tested compounds demonstrated moderate antiradical activity in DPPH test (up to EC50 16 mu M). The same compounds strongly inhibited soybean lipoxygenase (up to IC50 0.4 mu M) and Fe2+- and Fe3+-induced lipid peroxidation (LP) of rat brain cortex homogenate (up to IC50 0.3 mu M). All tested isoxazole derivatives promoted the phosphorylating respiratory activity simultaneously with maximal stimulated respiratory activity of mitochondria and do not reveal any toxicity towards the primary culture of rat cortex neurons. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.040

文献信息

• Synthesis and biological evaluation of novel 5-hydroxylaminoisoxazole derivatives as lipoxygenase inhibitors and metabolism enhancing agents
  作者：Elena B. Averina、Dmitry A. Vasilenko、Yulia A. Gracheva、Yuri K. Grishin、Eugene V. Radchenko、Vladimir V. Burmistrov、Gennady M. Butov、Margarita E. Neganova、Tatyana P. Serkova、Olga M. Redkozubova、Elena F. Shevtsova、Elena R. Milaeva、Tamara S. Kuznetsova、Nikolay S. Zefirov

  DOI：10.1016/j.bmc.2015.12.040

  日期：2016.2

  A versatile synthesis of novel 5-hydroxylaminoisoxazoles bearing adamantane moieties has been accomplished using the heterocyclization reactions of readily available unsaturated esters by the treatment with tetranitromethane in the presence of triethylamine and subsequent reduction of resulting 5-nitroisoxazoles by SnCl2 with the participation of THF. A number of obtained isoxazole derivatives were evaluated for their antioxidative activity, inhibition of lipoxygenases and impact on the rat liver mitochondria. The majority of tested compounds demonstrated moderate antiradical activity in DPPH test (up to EC50 16 mu M). The same compounds strongly inhibited soybean lipoxygenase (up to IC50 0.4 mu M) and Fe2+- and Fe3+-induced lipid peroxidation (LP) of rat brain cortex homogenate (up to IC50 0.3 mu M). All tested isoxazole derivatives promoted the phosphorylating respiratory activity simultaneously with maximal stimulated respiratory activity of mitochondria and do not reveal any toxicity towards the primary culture of rat cortex neurons. (c) 2015 Elsevier Ltd. All rights reserved.