3-({2-[2-(3-methoxyphenyl)ethyl]phenoxy}methyl)pyridine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-({2-[2-(3-methoxyphenyl)ethyl]phenoxy}methyl)pyridine
• 英文别名: 3-((2-(3-Methoxyphenethyl)phenoxy)methyl)pyridine；3-[[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl]pyridine
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: REDYWFZNRVYCRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲氧基氯苄 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 48.0h， 生成 3-({2-[2-(3-methoxyphenyl)ethyl]phenoxy}methyl)pyridine
  参考文献：
  名称：

  Arylmethyloxyphenyl Derivatives:  Small Molecules Displaying P-Glycoprotein Inhibition

  摘要：

  Some arylmethyloxyphenyl derivatives were prepared as simplified structures of analogous arylpiperazines with high affinity toward dopaminergic D-2 and serotonergic 5-HT1A receptors and inhibiting P-glycoprotein (P-gp). The compounds 5b and 8b displayed good P-gp inhibition activity measured as [H-3] vinblastine transport inhibition in the Caco-2 cell monolayer and intracellular doxorubicin accumulation in MCF7/Adr cells by flow cytometry. Compounds 5b and 8b also inhibited, dose-dependently, ATP-ase activation induced by P-gp substrate vinblastine.

  DOI：

  10.1021/jm060639z

文献信息

• 1-PHENYLALCOXY-2-BETA-PHENYLETHYL DERIVATIVES AS P-GLYCOPROTEIN (P-GP) INHIBITORS USEFUL IN DRUG RESISTANCE EVENTS
  申请人：Berardi Francesco

  公开号：US20090093493A1

  公开（公告）日：2009-04-09

  The invention relates to a new class of compounds, which are 1-phenylalcoxy-2-β-phenylethyl derivatives, as P-glycoprotein (P-GP) inhibitors. These compounds are useful in drug resistance events. They have been shown able to inhibit in a dose-dependent manner Glycoprotein-P (P-gp) activity in cell lines in which the expression of said glycoprotein is very high, like Caco-2 (human colon cancer) cells and MCF7/Adr (adriamycin-resistant human breast carcinoma) cells. The invention also relates to methods of production and the utilization of such compounds as medicaments useful in the treatment of states linked to the difficulty for some drugs to cross the blood-brain barrier (BBB) and generally within the context of the problems of drug resistance induced by chemotherapy agents.

  该发明涉及一类新化合物，即1-苯基羟基-2-β-苯乙基衍生物，作为P-糖蛋白（P-GP）抑制剂。这些化合物在药物耐药事件中很有用。已经证明它们能够以剂量依赖的方式抑制细胞系中的糖蛋白-P（P-gp）活性，其中所述糖蛋白的表达非常高，如Caco-2（人类结肠癌）细胞和MCF7/Adr（阿霉素耐药的人类乳腺癌）细胞。该发明还涉及生产方法和利用这类化合物作为药物的方法，用于治疗与某些药物跨越血脑屏障（BBB）困难相关的状态，以及在化疗药物引起的药物耐药问题背景下的一般情况。
• Arylmethyloxyphenyl Derivatives:  Small Molecules Displaying P-Glycoprotein Inhibition
  作者：Nicola Antonio Colabufo、Francesco Berardi、Roberto Perrone、Simona Rapposelli、Maria Digiacomo、Aldo Balsamo

  DOI：10.1021/jm060639z

  日期：2006.11.1

  Some arylmethyloxyphenyl derivatives were prepared as simplified structures of analogous arylpiperazines with high affinity toward dopaminergic D-2 and serotonergic 5-HT1A receptors and inhibiting P-glycoprotein (P-gp). The compounds 5b and 8b displayed good P-gp inhibition activity measured as [H-3] vinblastine transport inhibition in the Caco-2 cell monolayer and intracellular doxorubicin accumulation in MCF7/Adr cells by flow cytometry. Compounds 5b and 8b also inhibited, dose-dependently, ATP-ase activation induced by P-gp substrate vinblastine.