(R)-4-(3,4-diethoxybenzyl)dihydrofuran-2-one | 1426297-78-0

• 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-(3,4-diethoxybenzyl)dihydrofuran-2-one
• 英文别名: (4R)-4-[(3,4-diethoxyphenyl)methyl]oxolan-2-one
• CAS: 1426297-78-0
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: BIHAYRKIWFZTBZ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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-(3,4-diethoxybenzyl)dihydrofuran-2-one 在 六甲基磷酰三胺 、 氢气 、 palladium(II) hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 41.5h， 生成 (3R,4R)-4-[(3,4-diethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)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：

  3,4-二乙氧基苯甲醇 在 盐酸 、 lithium aluminium tetrahydride 、 lithium hydroxide monohydrate 、 Amano lipase-PS 、 水 、 sodium hydride 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醚 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 123.0h， 生成 (R)-4-(3,4-diethoxybenzyl)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

文献信息

• Synthesis and antitumor evaluation of arctigenin derivatives based on antiausterity strategy
  作者：Naoki Kudou、Akira Taniguchi、Kenji Sugimoto、Yuji Matsuya、Masashi Kawasaki、Naoki Toyooka、Chika Miyoshi、Suresh Awale、Dya Fita Dibwe、Hiroyasu Esumi、Shigetoshi Kadota、Yasuhiro Tezuka

  DOI：10.1016/j.ejmech.2012.11.031

  日期：2013.2

  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.