(E)-3-[4-(diethylamino)phenyl]-1-[3-(4-phenyltriazol-1-yl)phenyl]prop-2-en-1-one | 1620154-31-5

• 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: (E)-3-[4-(diethylamino)phenyl]-1-[3-(4-phenyltriazol-1-yl)phenyl]prop-2-en-1-one
• CAS: 1620154-31-5
• 化学式: C₂₇H₂₆N₄O
• 分子量: 422.53
• InChiKey: DVXLONVAZYJZKC-OBGWFSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 在 copper(II) sulfate 、 sodium ascorbate 、 potassium hydroxide 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 15.0h， 生成 (E)-3-[4-(diethylamino)phenyl]-1-[3-(4-phenyltriazol-1-yl)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of diethylamino-curcumin mimics with substituted triazolyl groups and their sensitization effect of TRAIL against brain cancer cells

  摘要：

  A newly designed curcumin mimic library (11a-11k) with 2-ethylamino groups in a chalcone structure and variously substituted triazole groups as side chains was synthesized using the Huisgen 1,3-cycloaddition reaction between various alkynes (a-k) and an intermediate (10), with CuSO4 and sodium ascorbate in a solution mixture of chloroform, ethanol, and water (5:3:1) at room temperature for 5 h. In the lactate dehydrogenase (LDH) release assay involving co-treatment with tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) and/or synthetic curcumin derivatives using TRAILresistant human CRT-MG astroglioma cells, the novel curcumin mimic library was found to effectively stimulate the cytotoxicity of TRAIL, causing mild cytotoxicity when administered alone. In particular, 11a and 11j are promising candidates for TRAIL-sensitizers with potential use in combination chemotherapy for brain tumors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.098