5-chloropentyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate | 1208863-60-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-chloropentyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1208863-60-8
• 化学式: C₁₆H₂₁ClO₄
• 分子量: 312.793
• InChiKey: ROHVQKGHOSFOBI-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  5-氨基-1-戊醇 、 5-chloropentyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 5-((5-hydroxypentyl)amino)pentyl (E)-3-(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  Structure−Activity Relationships Studies in a Series of N,N-Bis(alkanol)amine Aryl Esters as P-Glycoprotein (Pgp) Dependent Multidrug Resistance (MDR) Inhibitors

  摘要：

  As a continuation Or a previous research, a series of N,N-bis(alkanol)amine aryl esters, as Pgp-dependent MDR inhibitors, was; designed and synthesized. The aromatic ester portions are suitably modulated, and new aryl rings (Ar-1 and Ar-2) were combined with trans-3-(3,4,5-trimethoxyphenyl)-vinyl, 3,4,5-trimethoxybenzyl and anthracene moieties that were present in the most potent previously Studied compounds. The new compounds showed I wide range of potencies and efficacies Oil doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay. Selected compounds (5, 6, 8, 9, and 21) were further Studied, evaluating their action on doxorubicin cytotoxicity potentiation oil K562 cells; they significantly enhanced doxorubicin cytotoxicity oil K562/DOX cells, confirming the results obtained with pirarubicin. Compound 9 Shows file Most promising properties as it was able to nearly completely reverse Pgp-dependent pirarubicin extrusion at nanomolar closes and increased the cytotoxicity of doxorubicin with a reversal fold (RF) of 19.1 at 3 mu M dose.

  DOI：

  10.1021/jm9016174
• 作为产物：
  描述：

  5-氯-1-戊醇 、 3,4-二甲氧基肉桂酰氯 以 氯仿 为溶剂， 生成 5-chloropentyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Structure−Activity Relationships Studies in a Series of N,N-Bis(alkanol)amine Aryl Esters as P-Glycoprotein (Pgp) Dependent Multidrug Resistance (MDR) Inhibitors

  摘要：

  As a continuation Or a previous research, a series of N,N-bis(alkanol)amine aryl esters, as Pgp-dependent MDR inhibitors, was; designed and synthesized. The aromatic ester portions are suitably modulated, and new aryl rings (Ar-1 and Ar-2) were combined with trans-3-(3,4,5-trimethoxyphenyl)-vinyl, 3,4,5-trimethoxybenzyl and anthracene moieties that were present in the most potent previously Studied compounds. The new compounds showed I wide range of potencies and efficacies Oil doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay. Selected compounds (5, 6, 8, 9, and 21) were further Studied, evaluating their action on doxorubicin cytotoxicity potentiation oil K562 cells; they significantly enhanced doxorubicin cytotoxicity oil K562/DOX cells, confirming the results obtained with pirarubicin. Compound 9 Shows file Most promising properties as it was able to nearly completely reverse Pgp-dependent pirarubicin extrusion at nanomolar closes and increased the cytotoxicity of doxorubicin with a reversal fold (RF) of 19.1 at 3 mu M dose.

  DOI：

  10.1021/jm9016174

文献信息

• Structure−Activity Relationships Studies in a Series of <i>N</i>,<i>N</i>-Bis(alkanol)amine Aryl Esters as P-Glycoprotein (Pgp) Dependent Multidrug Resistance (MDR) Inhibitors
  作者：Cecilia Martelli、Marcella Coronnello、Silvia Dei、Dina Manetti、Francesca Orlandi、Serena Scapecchi、Maria Novella Romanelli、Milena Salerno、Enrico Mini、Elisabetta Teodori

  DOI：10.1021/jm9016174

  日期：2010.2.25

  As a continuation Or a previous research, a series of N,N-bis(alkanol)amine aryl esters, as Pgp-dependent MDR inhibitors, was; designed and synthesized. The aromatic ester portions are suitably modulated, and new aryl rings (Ar-1 and Ar-2) were combined with trans-3-(3,4,5-trimethoxyphenyl)-vinyl, 3,4,5-trimethoxybenzyl and anthracene moieties that were present in the most potent previously Studied compounds. The new compounds showed I wide range of potencies and efficacies Oil doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay. Selected compounds (5, 6, 8, 9, and 21) were further Studied, evaluating their action on doxorubicin cytotoxicity potentiation oil K562 cells; they significantly enhanced doxorubicin cytotoxicity oil K562/DOX cells, confirming the results obtained with pirarubicin. Compound 9 Shows file Most promising properties as it was able to nearly completely reverse Pgp-dependent pirarubicin extrusion at nanomolar closes and increased the cytotoxicity of doxorubicin with a reversal fold (RF) of 19.1 at 3 mu M dose.