(R)-4-(3-ethoxy-4-methoxybenzyl)dihydrofuran-2-one | 1426297-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-4-(3-ethoxy-4-methoxybenzyl)dihydrofuran-2-one
• 英文别名: (4R)-4-[(3-ethoxy-4-methoxyphenyl)methyl]oxolan-2-one
• CAS: 1426297-76-8
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: WQOVREYSNGLFDV-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(溴甲基)-2-甲氧基-1-苯基甲氧基苯 、 (R)-4-(3-ethoxy-4-methoxybenzyl)dihydrofuran-2-one 在 六甲基磷酰三胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 21.5h， 以44%的产率得到(3R,4R)-3-(4-benzyloxy-3-methoxybenzyl)-4-(3-ethoxy-4-methoxybenzyl)dihydrofuran-2-one
  参考文献：
  名称：

  Synthesis and antitumor evaluation of arctigenin derivatives based on antiausterity strategy

  摘要：

  A series of new (-)-arctigenin derivatives with variably modified O-alkyl groups were synthesized and their preferential cytotoxicity was evaluated against human pancreatic cancer cell line PANC-1 under nutrient-deprived conditions. The results showed that monoethoxy derivative 4i (PC50, 0.49 mu M), diethoxy derivative 4h (PC50, 0.66 mu M), and triethoxy derivative 4m (PC50, 0.78. mu M) showed the preferential cytotoxicities under nutrient-deprived conditions, which were identical to or more potent than (-)-arctigenin (1) (PC50, 0.80 mu M). Among them, we selected the triethoxy derivative 4m and examined its in vivo antitumor activity using a mouse xenograft model. Triethoxy derivative 4m exhibited also in vivo antitumor activity with the potency identical to or slightly more than (-)-arctigenin (1). These results would suggest that a modification of (-)-arctigenin structure could lead to a new drug based on the antiausterity strategy. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.031