9-chloro-2-ethyl-acridine | 65753-75-5

• 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: 9-chloro-2-ethyl-acridine
• 英文别名: 2-ethyl-9-chloro-acridine；2-Aethyl-9-chlor-acridin；9-chloro-2-ethylacridine
• CAS: 65753-75-5
• 化学式: C₁₅H₁₂ClN
• 分子量: 241.72
• InChiKey: KWVNPSREFRJFNV-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88.5 °C
• 沸点：
  402.1±18.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-chloro-2-ethyl-acridine 在 氢氧化钾 、 镍 、 苯 作用下， 生成 2-ethylacridine
  参考文献：
  名称：

  THE SYNTHESIS OF 1-ETHYL-, 2-ETHYL-, 3-ETHYL- AND 4-ETHYL-ACRIDINE¹

  摘要：

  DOI：

  10.1021/jo01369a018
• 作为产物：
  描述：

  2-氯苯甲酸 在 铜 、 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 9-chloro-2-ethyl-acridine
  参考文献：
  名称：

  Synthesis and biological evaluation of benzimidazole acridine derivatives as potential DNA-binding and apoptosis-inducing agents

  摘要：

  The discovery of new effective DNA-targeted antitumor agent is needed because of their clinical significance. As acridines can intercalate into DNA and benzimidazoles have the ability to bind in the DNA minor groove, a series of novel benzimidazole acridine derivatives were designed and synthesized to be new DNA-targeted compounds. MTT assay indicated that most of the synthesized compounds displayed good antiproliferative activity, among which compound 8l demonstrated the highest activity against both K562 and HepG-2 cells. Further experiments showed that 8l displayed good DNA-binding capability and inhibited topoisomerase I activity. Moreover, compound 8l could induce apoptosis in K562 cell lines through mitochondrial pathway. These data suggested that compound 8l might be potential as new DNA-binding and apoptosis-inducing antitumor agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.036

文献信息

• Synthesis and biological evaluation of benzimidazole acridine derivatives as potential DNA-binding and apoptosis-inducing agents
  作者：Chunmei Gao、Bin Li、Bin Zhang、Qinsheng Sun、Lulu Li、Xi Li、Changjun Chen、Chunyan Tan、Hongxia Liu、Yuyang Jiang

  DOI：10.1016/j.bmc.2015.02.036

  日期：2015.4

  The discovery of new effective DNA-targeted antitumor agent is needed because of their clinical significance. As acridines can intercalate into DNA and benzimidazoles have the ability to bind in the DNA minor groove, a series of novel benzimidazole acridine derivatives were designed and synthesized to be new DNA-targeted compounds. MTT assay indicated that most of the synthesized compounds displayed good antiproliferative activity, among which compound 8l demonstrated the highest activity against both K562 and HepG-2 cells. Further experiments showed that 8l displayed good DNA-binding capability and inhibited topoisomerase I activity. Moreover, compound 8l could induce apoptosis in K562 cell lines through mitochondrial pathway. These data suggested that compound 8l might be potential as new DNA-binding and apoptosis-inducing antitumor agents. (C) 2015 Elsevier Ltd. All rights reserved.
• THE SYNTHESIS OF 1-ETHYL-, 2-ETHYL-, 3-ETHYL- AND 4-ETHYL-ACRIDINE¹
  作者：LEWIS J. SARGENT

  DOI：10.1021/jo01369a018

  日期：1954.4