(3R,4R)-3-(4-benzyloxy-3-hydroxybenzyl)-4-(3,4-dimethoxybenzyl)dihydrofuran-2-one | 1426297-61-1

• 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-hydroxybenzyl)-4-(3,4-dimethoxybenzyl)dihydrofuran-2-one
• 英文别名: (3R,4R)-3-(4-(benzyloxy)-3-hydroxybenzyl)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one；(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-hydroxy-4-phenylmethoxyphenyl)methyl]oxolan-2-one
• CAS: 1426297-61-1
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: PZTPLHNGSCAOID-FCHUYYIVSA-N

物化性质

• 沸点：
  647.8±50.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-(4-benzyloxy-3-hydroxybenzyl)-4-(3,4-dimethoxybenzyl)dihydrofuran-2-one 在 氢气 、 palladium(II) hydroxide 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-hydroxy-3-(2-hydroxyethoxy)phenyl]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：

  牛蒡子苷元 在 吡啶 、 aluminum (III) chloride 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 25.0h， 生成 (3R,4R)-3-(4-benzyloxy-3-hydroxybenzyl)-4-(3,4-dimethoxybenzyl)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

• 木脂素衍生物、其制备方法及用途
  申请人：中国科学院上海药物研究所

  公开号：CN115215821A

  公开（公告）日：2022-10-21

  本发明公开了一种木脂素衍生物、其制备方法及用途，所述木脂素衍生物结构如式I所示，式中，各取代基的定义如说明书和权利要求书中所述。本发明的木脂素衍生物，能够作为线粒体呼吸链复合物I抑制剂，抑制线粒体的氧化磷酸化作用及ATP的生成，用于预防和/或治疗与线粒体呼吸链复合物I活性或表达升高、或者线粒体氧化磷酸化作用增强相关的疾病。
• 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.