N-[1-(4-bromophenyl)-3-(4-methoxyphenyl)prop-2-enylidene]hydroxylamine | 936327-44-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-[1-(4-bromophenyl)-3-(4-methoxyphenyl)prop-2-enylidene]hydroxylamine
• CAS: 936327-44-5
• 化学式: C₁₆H₁₄BrNO₂
• 分子量: 332.197
• InChiKey: DZISLAFUCQZBIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (E)-1-(4-溴苯基)-3-(4-甲氧基苯基)丙-2-烯-1-酮 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 生成 N-[1-(4-bromophenyl)-3-(4-methoxyphenyl)prop-2-enylidene]hydroxylamine
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of chalcone oxime derivatives as potential immunosuppressive agents

  摘要：

  A series of deoxybenzoin oximes were recently reported as potent immunosuppressive agents by our group. In order to continue the original research for potential immunosuppressive agents with high efficacy and low toxicity, we synthesized a series of new chalcone oximes and evaluated them for their cytotoxicities and immunosuppressive activities. Among the synthesized compounds, chalcone oximes 25 and 27 exhibited lower cytotoxicities and higher inhibitory activities on anti-CD3/anti-CD28 co-stimulated lymph node cells than other compounds. Specially, compound 27 displayed 200-fold lower cytotoxicity (CC50 = 2174.39 mu M) than cyclosporin A (CC50 = 10.10 mu M) and showed SI value (SI = 176.69) close to cyclosporin A (SI = 154.13). Besides, the preliminary mechanism of inhibition effect of compounds 25 and 27 was also detected by flow cytometry, and the compounds exerted immunosuppressive activities via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Also, the deep mechanism of apoptosis was detected by Western blot analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.080

文献信息

• Design, synthesis, and biological evaluation of chalcone oxime derivatives as potential immunosuppressive agents
  作者：Yin Luo、Ran Song、Yao Li、Shuai Zhang、Zhi-Jun Liu、Jie Fu、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2012.03.080

  日期：2012.5

  A series of deoxybenzoin oximes were recently reported as potent immunosuppressive agents by our group. In order to continue the original research for potential immunosuppressive agents with high efficacy and low toxicity, we synthesized a series of new chalcone oximes and evaluated them for their cytotoxicities and immunosuppressive activities. Among the synthesized compounds, chalcone oximes 25 and 27 exhibited lower cytotoxicities and higher inhibitory activities on anti-CD3/anti-CD28 co-stimulated lymph node cells than other compounds. Specially, compound 27 displayed 200-fold lower cytotoxicity (CC50 = 2174.39 mu M) than cyclosporin A (CC50 = 10.10 mu M) and showed SI value (SI = 176.69) close to cyclosporin A (SI = 154.13). Besides, the preliminary mechanism of inhibition effect of compounds 25 and 27 was also detected by flow cytometry, and the compounds exerted immunosuppressive activities via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Also, the deep mechanism of apoptosis was detected by Western blot analysis. (C) 2012 Elsevier Ltd. All rights reserved.