3-[methyl-[3-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxypropyl]amino]propyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate | 1209049-62-6

• 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: 3-[methyl-[3-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxypropyl]amino]propyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1209049-62-6
• 化学式: C₃₀H₃₉NO₉
• 分子量: 557.641
• InChiKey: UZWBTKVNLXACMQ-IFQMDVHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-((3-hydroxypropyl)(methyl)amino)propyl (E)-3-(3,4-dimethoxyphenyl)acrylate 、 3,4,5-三甲氧基肉桂酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-[methyl-[3-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxypropyl]amino]propyl (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.