2-butyl-9-chloroacridine | 55751-64-9

• 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: 2-butyl-9-chloroacridine
• 英文别名: 2-butyl-9-chloro-acridine
• CAS: 55751-64-9
• 化学式: C₁₇H₁₆ClN
• 分子量: 269.774
• InChiKey: ZXXCUIKOWOAXEF-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  424.4±18.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (1H-苯并咪唑-2-亚甲基)胺 、 2-butyl-9-chloroacridine 反应 3.0h， 以45%的产率得到N-((1H-benzo[d]imidazol-2-yl)methyl)-2-butylacridin-9-amine
  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
• 作为产物：
  描述：

  4-正丁基苯胺 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 2-butyl-9-chloroacridine
  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

• 4-酰胺基苯并咪唑吖啶类化合物及其制备方 法和用途
  申请人：清华大学深圳研究生院

  公开号：CN106045973B

  公开（公告）日：2019-03-22

  本发明提供了4‑酰胺基苯并咪唑吖啶类化合物及其制备方法和用途，其中，该化合物为具有式I所示结构式的4‑酰胺基苯并咪唑吖啶类化合物或具有式I所示结构式的4‑酰胺基苯并咪唑吖啶类化合物的药学上可接受的盐、酯或者溶剂合物，其中，R1为不同位置取代的H、OH、OC2H5、OCH2CH2CH3、OCH(CH3)2、OCH(CH3)CH2CH3、OC(CH3)3、OCH2CH2CH2CH3、F、Cl、Br、CF3、NH2、NO2、COOH、NHCOCH3、OCH3、CH3、CH2CH3、CH2CH2CH3、CH3CHCH3、CH3CHCH2CH3、(CH3)3C、CH2CH2CH2CH3，R2为不同位置取代的‑NH‑，NHCH2、NHCH2CH2、NHCH2CH2CH2、NHCONH、NHCOCH2NH、NHCOCH2NH、或OCH2。本发明的该化合物能够有效抑制拓扑异构酶、抑制聚腺苷二磷酸核糖聚合酶(PARP)酶、抑制真核生物肿瘤细胞增殖、预防或治疗肿瘤。
• ACHESON R. M.; BOLTON R. G., J. CHEM. SOC. PERKIN TRANS. <JCPK-BH>, 1975, PART 1, NO 7, 650-653
  作者：ACHESON R. M.、 BOLTON R. G.

  DOI：——

  日期：——
• 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.
• Design, synthesis and biological evaluation of 4-amidobenzimidazole acridine derivatives as dual PARP and Topo inhibitors for cancer therapy
  作者：Zigao Yuan、Shaopeng Chen、Changjun Chen、Jiwei Chen、Chengken Chen、Qiuzi Dai、Chunmei Gao、Yuyang Jiang

  DOI：10.1016/j.ejmech.2017.07.050

  日期：2017.9

  PARP-1 could repair the DNA damages induced by Topo inhibitors, therefore inhibiting Topo and PARP-1 simultaneously might be able to overcome resistance and improve outcomes. In this study a series of 4-amidobenzimidazole acridines were designed and synthesized as dual Topo and PARP-1 inhibitors. Compound 111 displayed good inhibitory activities against Topo and PARP-1, as well as significantly inhibited cancer cells proliferation. Further mechanistic evaluations indicated that 111 treatment in MCF-7 cells induced accumulated DNA double-strand breaks, prompted remarkable apoptosis, and caused prominent GO/G1 cell cycle arrest. Moreover, 111 greatly suppressed tumor growth in mice, and displayed favorable metabolic properties in liver microsomes. Our study suggested that single agents inhibiting Topo and PARP concurrently might be an alternative for cancer therapy and 111 represented a potential lead compound for development of antitumor agents. (C) 2017 Elsevier Masson SAS. All rights reserved.