N-[3-(acridin-9-ylamino)-5-(hydroxymethyl)phenyl]-5,5-dimethyl-4-oxohexanamide | 1384959-22-1

• 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: N-[3-(acridin-9-ylamino)-5-(hydroxymethyl)phenyl]-5,5-dimethyl-4-oxohexanamide
• CAS: 1384959-22-1
• 化学式: C₂₈H₂₉N₃O₃
• 分子量: 455.557
• InChiKey: VJILFOJVAOWKHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.3
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methacrylamidohexanohydrazide 、 N-[3-(acridin-9-ylamino)-5-(hydroxymethyl)phenyl]-5,5-dimethyl-4-oxohexanamide 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以37%的产率得到N-[5-(N'-acridin-9-yl-hydrazinocarbonyl)-pentyl]-2-methyl-acrylamide
  参考文献：
  名称：

  Polymer conjugates of acridine-type anticancer drugs with pH-controlled activation

  摘要：

  Acridines are potent DNA-intercalating anticancer agents with high in vivo anticancer effectiveness, but also severe side effects. We synthesized five 9-anilinoacridine-type drugs and their conjugates with biocompatible water-soluble hydrazide polymer carrier. All of the synthesized acridine drugs retained their in vitro antiproliferative properties. Their polymer conjugates were sufficiently stable at pH 7.4 (model of pH in blood plasma) while releasing free drugs at pH 5.0 (model of pH in endosomes). After internalization of the conjugates, the free drugs were released and are visible in cell nuclei by fluorescence microscopy. Their intercalation ability was proven using a competitive ethidium bromide displacement assay. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.007
• 作为产物：
  描述：

  1-溴频哪酮 在 sodium methylate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 N-[3-(acridin-9-ylamino)-5-(hydroxymethyl)phenyl]-5,5-dimethyl-4-oxohexanamide
  参考文献：
  名称：

  Polymer conjugates of acridine-type anticancer drugs with pH-controlled activation

  摘要：

  Acridines are potent DNA-intercalating anticancer agents with high in vivo anticancer effectiveness, but also severe side effects. We synthesized five 9-anilinoacridine-type drugs and their conjugates with biocompatible water-soluble hydrazide polymer carrier. All of the synthesized acridine drugs retained their in vitro antiproliferative properties. Their polymer conjugates were sufficiently stable at pH 7.4 (model of pH in blood plasma) while releasing free drugs at pH 5.0 (model of pH in endosomes). After internalization of the conjugates, the free drugs were released and are visible in cell nuclei by fluorescence microscopy. Their intercalation ability was proven using a competitive ethidium bromide displacement assay. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.007

文献信息

• Polymer conjugates of acridine-type anticancer drugs with pH-controlled activation
  作者：Ondřej Sedláček、Martin Hrubý、Martin Studenovský、David Větvička、Jan Svoboda、Dana Kaňková、Jan Kovář、Karel Ulbrich

  DOI：10.1016/j.bmc.2012.05.007

  日期：2012.7

  Acridines are potent DNA-intercalating anticancer agents with high in vivo anticancer effectiveness, but also severe side effects. We synthesized five 9-anilinoacridine-type drugs and their conjugates with biocompatible water-soluble hydrazide polymer carrier. All of the synthesized acridine drugs retained their in vitro antiproliferative properties. Their polymer conjugates were sufficiently stable at pH 7.4 (model of pH in blood plasma) while releasing free drugs at pH 5.0 (model of pH in endosomes). After internalization of the conjugates, the free drugs were released and are visible in cell nuclei by fluorescence microscopy. Their intercalation ability was proven using a competitive ethidium bromide displacement assay. (C) 2012 Elsevier Ltd. All rights reserved.