(E)-3-(methyl-(5-((3-(3,4,5-trimethoxyphenyl)acryloyl)oxy)pentyl)amino)propyl anthracene-9-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (E)-3-(methyl-(5-((3-(3,4,5-trimethoxyphenyl)acryloyl)oxy)pentyl)amino)propyl anthracene-9-carboxylate
• 英文别名: (E)-3-(methyl(5-((3-(3,4,5-trimethoxyphenyl)acryloyl)oxy)pentyl)amino)propyl anthracene-9-carboxylate；GDE6；3-[methyl-[5-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxypentyl]amino]propyl anthracene-9-carboxylate
• 化学式: C₃₆H₄₁NO₇
• 分子量: 599.724
• InChiKey: MWPKBYPHINXLGS-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (E)-3-(3,4,5-Trimethoxy-phenyl)-acrylic acid 5-chloro-pentyl ester 在 4-二甲氨基吡啶 、 甲酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 49.0h， 生成 (E)-3-(methyl-(5-((3-(3,4,5-trimethoxyphenyl)acryloyl)oxy)pentyl)amino)propyl anthracene-9-carboxylate
  参考文献：
  名称：

  Multidrug resistance (MDR) reversers: High activity and efficacy in a series of asymmetrical N,N-bis(alkanol)amine aryl esters

  摘要：

  As a continuation of our research on potent and efficacious P-gp-dependent multidrug resistance (MDR) reversers, several new N,N-bis(alkanol)amine aryl esters were designed and synthesized, varying the aromatic moieties or the length of the methylenic chain. The new compounds were tested on doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay, where most of the new compounds were shown to be active. In particular the asymmetrical compounds, characterized by two linkers of different length, generally showed fairly high activities as MDR reversers. Some selected compounds (isomers 15-17) were further studied by evaluating their doxorubicin cytotoxicity enhancement (reversal fold, RF) on the K562/DOX cell line. The results of both pharmacological assays indicate that compounds 16 (GDE6) and 17 (GDE19) could be interesting leads for the development of new P-gp dependent MDR modulators. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.084

文献信息

• Multidrug resistance (MDR) reversers: High activity and efficacy in a series of asymmetrical N,N-bis(alkanol)amine aryl esters
  作者：Silvia Dei、Marcella Coronnello、Elisa Floriddia、Gianluca Bartolucci、Cristina Bellucci、Luca Guandalini、Dina Manetti、Maria Novella Romanelli、Milena Salerno、Ivan Bello、Enrico Mini、Elisabetta Teodori

  DOI：10.1016/j.ejmech.2014.09.084

  日期：2014.11

  As a continuation of our research on potent and efficacious P-gp-dependent multidrug resistance (MDR) reversers, several new N,N-bis(alkanol)amine aryl esters were designed and synthesized, varying the aromatic moieties or the length of the methylenic chain. The new compounds were tested on doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay, where most of the new compounds were shown to be active. In particular the asymmetrical compounds, characterized by two linkers of different length, generally showed fairly high activities as MDR reversers. Some selected compounds (isomers 15-17) were further studied by evaluating their doxorubicin cytotoxicity enhancement (reversal fold, RF) on the K562/DOX cell line. The results of both pharmacological assays indicate that compounds 16 (GDE6) and 17 (GDE19) could be interesting leads for the development of new P-gp dependent MDR modulators. (C) 2014 Elsevier Masson SAS. All rights reserved.