(E)-3-(4-((1-(2-ethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)prop-2-en-1-one

• 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: (E)-3-(4-((1-(2-ethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)prop-2-en-1-one
• 英文别名: (E)-3-[4-[[1-(2-ethylphenyl)triazol-4-yl]methoxy]phenyl]-1-(5-hydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)prop-2-en-1-one
• 化学式: C₃₁H₃₁N₃O₄
• 分子量: 509.605
• InChiKey: AKSQTFLOYZHLTJ-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(5-hydroxy-2,2-dimethylchroman-6-yl)ethanone 在 copper(l) iodide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.0h， 生成 (E)-3-(4-((1-(2-ethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, docking and ADMET studies of novel chalcone triazoles for anti-cancer and anti-diabetic activity

  摘要：

  A series of novel chalcone-triazole derivatives were synthesized and screened for in vitro anticancer activity on the human cancer cell lines IMR32 (neuroblastoma), HepG2 (hepatoma) and MCF-7 (breast adenocarcinoma), DU-145 (prostate carcinoma), and A549 (lung adenocarcinoma). Among the tested compounds, 4r showed the most promising anticancer activity in all the cell lines whereas, compounds 4c (IC50 65.86 mu M), 4e (IC50 66.28 mu M), 4o (IC50 35.81 mu M), 4q (IC50 50.82 mu M) and 4s (IC50 48.63 mu M) showed better activity than the standard doxorubicin (IC50 69.33 mu M) in A549 cell line alone. Rat intestinal a-glucosidase inhibitory activity of the synthesized derivatives showed 4m (IC50 67.77 mu M), 4p (IC50 74.94 in mu M) and 4s (IC50 102.10 mu M) as most active compared to others. The in silico docking of synthesized derivatives 4a-4t with DNA topoisomerase II alpha revealed the LibDock score in the range of 71.2623-118.29 whereas, compounds 4h, 4m, 4p and 4s with docking target a-glucosidase were in the range of 100.372-107.784. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.027