(3R,4R)-3-(4-benzyloxy-3-propoxybenzyl)-4-(3-ethoxy-4-methoxybenzyl)dihydrofuran-2-one | 1426297-85-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (3R,4R)-3-(4-benzyloxy-3-propoxybenzyl)-4-(3-ethoxy-4-methoxybenzyl)dihydrofuran-2-one
• 英文别名: (3R,4R)-4-[(3-ethoxy-4-methoxyphenyl)methyl]-3-[(4-phenylmethoxy-3-propoxyphenyl)methyl]oxolan-2-one
• CAS: 1426297-85-9
• 化学式: C₃₁H₃₆O₆
• 分子量: 504.623
• InChiKey: QSIHWBCNFHFPOD-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-(4-benzyloxy-3-propoxybenzyl)-4-(3-ethoxy-4-methoxybenzyl)dihydrofuran-2-one 在 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以56%的产率得到(3R,4R)-4-[(3-ethoxy-4-methoxyphenyl)methyl]-3-[(4-hydroxy-3-propoxyphenyl)methyl]oxolan-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
• 作为产物：
  描述：

  4-(benzyloxy)-3-propoxybenzaldehyde 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 三溴化磷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3R,4R)-3-(4-benzyloxy-3-propoxybenzyl)-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