(E)-3-(9-anthracenyl)-N,N-diethylacrylamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (E)-3-(9-anthracenyl)-N,N-diethylacrylamide
• 英文别名: (E)-3-anthracen-9-yl-N,N-diethylprop-2-enamide
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: KJHXEDCQZWGBIY-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Ethyl 3-(9-Anthryl)prop-2-enoate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 (E)-3-(9-anthracenyl)-N,N-diethylacrylamide
  参考文献：
  名称：

  Synthesis and antiproliferative action of a novel series of maprotiline analogues

  摘要：

  The synthesis of a diverse library of compounds structurally related to maprotiline, a norepinephrine reuptake transporter (NET) selective antidepressant which has recently been identified as a novel in vitro antiproliferative agent against Burkitt's lymphoma (BL) cell lines is reported. A series of 9,10-dihydro-9,10-ethanoanthracenes were synthesised with modifications to the bridge of the dihydroethanoanthracene structure and with alterations to the basic side chain. A number of compounds were found to reduce cell viability to a greater extent than maprotiline in BL cell lines. In addition a related series of novel 9-substituted anthracene compounds were investigated as intermediates in the synthesis of 9,10-dihydro-9,10-ethanoanthracenes. These compounds proved the most active from the screen and were found to exert a potent caspase-dependant apoptotic effect in the BL cell lines, while having minimal effect on the viability of peripheral blood mononuclear cells (PBMCs). Compounds also displayed activity in multi-drug resistant (MDR) cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.076

文献信息

• Synthesis and antiproliferative action of a novel series of maprotiline analogues
  作者：Y.M. McNamara、S.A. Bright、A.J. Byrne、S.M. Cloonan、T. McCabe、D.C. Williams、M.J. Meegan

  DOI：10.1016/j.ejmech.2013.10.076

  日期：2014.1

  The synthesis of a diverse library of compounds structurally related to maprotiline, a norepinephrine reuptake transporter (NET) selective antidepressant which has recently been identified as a novel in vitro antiproliferative agent against Burkitt's lymphoma (BL) cell lines is reported. A series of 9,10-dihydro-9,10-ethanoanthracenes were synthesised with modifications to the bridge of the dihydroethanoanthracene structure and with alterations to the basic side chain. A number of compounds were found to reduce cell viability to a greater extent than maprotiline in BL cell lines. In addition a related series of novel 9-substituted anthracene compounds were investigated as intermediates in the synthesis of 9,10-dihydro-9,10-ethanoanthracenes. These compounds proved the most active from the screen and were found to exert a potent caspase-dependant apoptotic effect in the BL cell lines, while having minimal effect on the viability of peripheral blood mononuclear cells (PBMCs). Compounds also displayed activity in multi-drug resistant (MDR) cells. (C) 2013 Elsevier Masson SAS. All rights reserved.