ethyl 1-(3-methoxybenzyl)-4-(3-methoxyphenyl)-1,4-dihydroquinolin-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 1-(3-methoxybenzyl)-4-(3-methoxyphenyl)-1,4-dihydroquinolin-3-carboxylate
• 英文别名: ethyl 4-(3-methoxyphenyl)-1-[(3-methoxyphenyl)methyl]-4H-quinoline-3-carboxylate
• 化学式: C₂₇H₂₇NO₄
• 分子量: 429.516
• InChiKey: ANYQZWFWLCMMGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-喹啉羧酸乙酯 在 copper(l) iodide 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 ethyl 1-(3-methoxybenzyl)-4-(3-methoxyphenyl)-1,4-dihydroquinolin-3-carboxylate
  参考文献：
  名称：

  Discovery of substituted 1,4-dihydroquinolines as novel class of ABCB1 modulators

  摘要：

  Transmembrane efflux pumps are one main cause for multidrug resistance (mdr) of cancer. One hopeful approach to combate the mdr has been the development of inhibitors of the efflux pump activity. A novel class of small-molecule inhibitors of the most important efflux pump ABCB1 (P-glycoprotein) has been discovered. Inhibitory activities are discussed in relation to substituent effects. Most active compounds have been evaluated in first bioanalytical studies to reverse the mdr of an anticancer drug. Cellular toxicity and ABCB1 substrate properties of the compounds were investigated. A cellular induction of relevant efflux pump protein expressions was not observed under inhibitor application, so that our compounds are perspective candidates for further preclinical studies. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.016

文献信息

• Discovery of substituted 1,4-dihydroquinolines as novel class of ABCB1 modulators
  作者：Marc Hemmer、Sören Krawczyk、Ina Simon、Hermann Lage、Andreas Hilgeroth

  DOI：10.1016/j.bmc.2015.05.016

  日期：2015.8

  Transmembrane efflux pumps are one main cause for multidrug resistance (mdr) of cancer. One hopeful approach to combate the mdr has been the development of inhibitors of the efflux pump activity. A novel class of small-molecule inhibitors of the most important efflux pump ABCB1 (P-glycoprotein) has been discovered. Inhibitory activities are discussed in relation to substituent effects. Most active compounds have been evaluated in first bioanalytical studies to reverse the mdr of an anticancer drug. Cellular toxicity and ABCB1 substrate properties of the compounds were investigated. A cellular induction of relevant efflux pump protein expressions was not observed under inhibitor application, so that our compounds are perspective candidates for further preclinical studies. (C) 2015 Elsevier Ltd. All rights reserved.
• Discovery of substituted 1,4-dihydroquinolines as novel promising class of P-glycoprotein inhibitors: First structure–activity relationships and bioanalytical studies
  作者：Marc Hemmer、Sören Krawczyk、Ina Simon、Andreas Hilgeroth

  DOI：10.1016/j.bmcl.2015.05.018

  日期：2015.8

  Multidrug resistance (mdr) is the most important problem in the therapeutical treatment of cancer. One central problem in the resistance proceeding is the expression of transmembrane efflux pumps which transport drugs out of the cells. We developed novel substituted 1,4-dihydroquinolines as inhibitors of the transmembrane efflux pump P-glycoprotein. Structure-activity relationships are discussed for this first series. Promising active inhibitors have been identified and first bioanalytical studies have been carried out to address questions of cellular toxicity, P-gp substrate as well as mdr reversal properties. (C) 2015 Elsevier Ltd. All rights reserved.