(E)-1-(2-(dodecyloxy)-6-hydroxyphenyl)-3-(4-(methoxymetho-xy)phenyl)prop-2-en-1-one | 1393845-58-3

• 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)-1-(2-(dodecyloxy)-6-hydroxyphenyl)-3-(4-(methoxymetho-xy)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-(2-dodecoxy-6-hydroxyphenyl)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 1393845-58-3
• 化学式: C₂₉H₄₀O₅
• 分子量: 468.634
• InChiKey: VHYWWOQOZTWGFA-DYTRJAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-(dodecyloxy)-6-hydroxyphenyl)-3-(4-(methoxymetho-xy)phenyl)prop-2-en-1-one 在 盐酸 、 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 水 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 6.0h， 生成 3-(dodecyloxy)-2-(1-hydroxy-3-(4-hydroxyphenyl)propyl)phenol
  参考文献：
  名称：

  A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB

  摘要：

  To define the structural features responsible for the activity of 2,4-dihydroxy-6-isopentyloxychalcone, a newly established inhibitor of LPS induced NF-kappa B activation (IC50 = 10 mu M), a series of its analogues was prepared and studied for their in vitro activities against LPS induced NF-kappa B inhibition in RAW 264.7 cells. Among the synthesized derivatives, (E)-1-(2-(decyloxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (1050 = 2.7 mu M) and (E)-1-(2-hydroxy-6-(tetradecyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (IC50 = 4.2 mu M) showed the most potent inhibition. The SAR studies confirmed that the length (C-8-C-14) and C-6 position of linear alkyl chain of ring A is an important factor for the inhibitory activity. Hydroxyl group and its location at 4-position on ring B is also important for the inhibition. The alpha,beta-unsaturated ketone moiety appears as a crucial motif of chalcones for the activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.019
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 potassium carbonate 、 sodium iodide 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 (E)-1-(2-(dodecyloxy)-6-hydroxyphenyl)-3-(4-(methoxymetho-xy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB

  摘要：

  To define the structural features responsible for the activity of 2,4-dihydroxy-6-isopentyloxychalcone, a newly established inhibitor of LPS induced NF-kappa B activation (IC50 = 10 mu M), a series of its analogues was prepared and studied for their in vitro activities against LPS induced NF-kappa B inhibition in RAW 264.7 cells. Among the synthesized derivatives, (E)-1-(2-(decyloxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (1050 = 2.7 mu M) and (E)-1-(2-hydroxy-6-(tetradecyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (IC50 = 4.2 mu M) showed the most potent inhibition. The SAR studies confirmed that the length (C-8-C-14) and C-6 position of linear alkyl chain of ring A is an important factor for the inhibitory activity. Hydroxyl group and its location at 4-position on ring B is also important for the inhibition. The alpha,beta-unsaturated ketone moiety appears as a crucial motif of chalcones for the activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.019