4-((E)-2-(4-((E)-4-hydroxystyryl)-1H-1,2,3-triazol-1-yl)vinyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-((E)-2-(4-((E)-4-hydroxystyryl)-1H-1,2,3-triazol-1-yl)vinyl)phenol
• 英文别名: 4-[(E)-2-[1-[(E)-2-(4-hydroxyphenyl)ethenyl]triazol-4-yl]ethenyl]phenol
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: BDNLHAJESVRTPT-DWOQSGHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-tert-butyldimethylsiloxycinnamic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 Oxone 、 copper(l) iodide 、 copper(ll) sulfate pentahydrate 、 三乙胺氢溴酸盐 、 sodium ascorbate 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 5.5h， 生成 4-((E)-2-(4-((E)-4-hydroxystyryl)-1H-1,2,3-triazol-1-yl)vinyl)phenol
  参考文献：
  名称：

  Triazole-curcuminoids: A new class of derivatives for ‘tuning’ curcumin bioactivities?

  摘要：

  Curcumin is a unique blend of pharmacophores responsible for the pleiotropy of this natural pigment. In the present study we have replaced the 1,3-dicarbonyl moiety with a 1,2,3-triazole ring to furnish a new class of triazole-curcuminoids as a possible strategy to generate new compounds with different potency and selectivity compared to curcumin. We obtained a proof-of-principle library of 28 compounds tested for their cytotoxicity (SY-SY5Y and HeLa cells) and for their ability to inhibit NF-kappa B. Furthermore, we also generated 1,3-dicarbonyl curcuminoids of selected click compounds. Triazole-curcuminoids lost their ability to be Michael's acceptors, yet maintained some of the features of the parent compounds and disclosed new ones. In particular, we found that some compounds were able to inhibit NF-kappa B without showing cytotoxicity, while others, unlike curcumin, activated NF-kappa B signalling. This validates the hypothesis that click libraries can be used to investigate the biological activities of curcumin as well as generate analogs with selected features. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.044

文献信息

• Triazole-curcuminoids: A new class of derivatives for ‘tuning’ curcumin bioactivities?
  作者：Diego Caprioglio、Simone Torretta、Maila Ferrari、Cristina Travelli、Ambra A. Grolla、Fabrizio Condorelli、Armando A. Genazzani、Alberto Minassi

  DOI：10.1016/j.bmc.2015.11.044

  日期：2016.1

  Curcumin is a unique blend of pharmacophores responsible for the pleiotropy of this natural pigment. In the present study we have replaced the 1,3-dicarbonyl moiety with a 1,2,3-triazole ring to furnish a new class of triazole-curcuminoids as a possible strategy to generate new compounds with different potency and selectivity compared to curcumin. We obtained a proof-of-principle library of 28 compounds tested for their cytotoxicity (SY-SY5Y and HeLa cells) and for their ability to inhibit NF-kappa B. Furthermore, we also generated 1,3-dicarbonyl curcuminoids of selected click compounds. Triazole-curcuminoids lost their ability to be Michael's acceptors, yet maintained some of the features of the parent compounds and disclosed new ones. In particular, we found that some compounds were able to inhibit NF-kappa B without showing cytotoxicity, while others, unlike curcumin, activated NF-kappa B signalling. This validates the hypothesis that click libraries can be used to investigate the biological activities of curcumin as well as generate analogs with selected features. (C) 2015 Elsevier Ltd. All rights reserved.