1-(5-bromopentyloxy)-2-[2-(3-methoxyphenyl)ethyl]benzene | 1092679-13-4

• 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: 1-(5-bromopentyloxy)-2-[2-(3-methoxyphenyl)ethyl]benzene
• 英文别名: 1-(5-Bromopentoxy)-2-[2-(3-methoxyphenyl)ethyl]benzene
• CAS: 1092679-13-4
• 化学式: C₂₀H₂₅BrO₂
• 分子量: 377.321
• InChiKey: WJVKAOVHXVYXHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-bromopentyloxy)-2-[2-(3-methoxyphenyl)ethyl]benzene 、 1-(4-fluorophenyl)piperazine dihydrochloride 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 5-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}pentyl-4-(4'-fluorophenyl)piperazine
  参考文献：
  名称：

  2-[(3-Methoxyphenylethyl)phenoxy]-Based ABCB1 Inhibitors: Effect of Different Basic Side-Chains on Their Biological Properties

  摘要：

  Recently, 2-[(3-methoxyphenylethyl)phenoxy]-moiety has been selected for the design and synthesis of new small ABCB1 inhibitors. In the present paper, this moiety has been linked through a spacer of 2-5 carbon atoms to the nitrogen of three different basic nuclei such as: (i) N-4-arylpiperazine, (ii) N-4-methylpiperazine, and (iii) 6,7-dimethoxytctrahydroisoquinoline. The results demonstrated that all the selected basic nuclei were well tolerated and that, globally, the best inhibitory activity for each series was obtained when the spacer between the 2-[(3-methoxyphenylethyl)phenoxy]moiety and the basic nucleus consisted of a four-carbon chain. Among the synthesized compounds, N-4-methylpiperazine- 10C (IC50 = 0.15 W) and tetrahydroisoquinoline-derivatives 11c (IC50 = 0.08 W) with the spacer n = 4 for both series, displayed the best potency to inhibit ABCB1 activity. Moreover, for each compound, the ABCB1 interacting mechanism has been evaluated by three combined biological assays. N-4-methylpiperazine- (10a-d) and tetrahydroisoquinoline-(11a-d) derivatives were Cyclosporin A-like ABCB1 nontransported substrates.

  DOI：

  10.1021/jm800928j
• 作为产物：
  描述：

  1,5-二溴戊烷 、 2-[2-(3-甲氧基苯基)乙基]苯酚 在 氢氧化钾 作用下， 以 叔丁醇 为溶剂， 反应 0.25h， 以33%的产率得到1-(5-bromopentyloxy)-2-[2-(3-methoxyphenyl)ethyl]benzene
  参考文献：
  名称：

  2-[(3-Methoxyphenylethyl)phenoxy]-Based ABCB1 Inhibitors: Effect of Different Basic Side-Chains on Their Biological Properties

  摘要：

  Recently, 2-[(3-methoxyphenylethyl)phenoxy]-moiety has been selected for the design and synthesis of new small ABCB1 inhibitors. In the present paper, this moiety has been linked through a spacer of 2-5 carbon atoms to the nitrogen of three different basic nuclei such as: (i) N-4-arylpiperazine, (ii) N-4-methylpiperazine, and (iii) 6,7-dimethoxytctrahydroisoquinoline. The results demonstrated that all the selected basic nuclei were well tolerated and that, globally, the best inhibitory activity for each series was obtained when the spacer between the 2-[(3-methoxyphenylethyl)phenoxy]moiety and the basic nucleus consisted of a four-carbon chain. Among the synthesized compounds, N-4-methylpiperazine- 10C (IC50 = 0.15 W) and tetrahydroisoquinoline-derivatives 11c (IC50 = 0.08 W) with the spacer n = 4 for both series, displayed the best potency to inhibit ABCB1 activity. Moreover, for each compound, the ABCB1 interacting mechanism has been evaluated by three combined biological assays. N-4-methylpiperazine- (10a-d) and tetrahydroisoquinoline-(11a-d) derivatives were Cyclosporin A-like ABCB1 nontransported substrates.

  DOI：

  10.1021/jm800928j