di-tert-butyl 4,4'-(but-2-ene-1,4-diyl)(E)-bis(piperazine-1-carboxylate) | 1351530-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: di-tert-butyl 4,4'-(but-2-ene-1,4-diyl)(E)-bis(piperazine-1-carboxylate)
• CAS: 1351530-63-6
• 化学式: C₂₂H₄₀N₄O₄
• 分子量: 424.584
• InChiKey: SKPRIJWVEDRIOT-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  65.56
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 4,4'-(but-2-ene-1,4-diyl)(E)-bis(piperazine-1-carboxylate) 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 1,4-bis(N-(2-(7-chloro-6-oxo-2H-dibenzo[cd,g]indazol-2-yl)ethyl)piperazin-1-yl)-2-trans-butene
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a novel series of bisintercalating DNA-binding piperazine-linked bisanthrapyrazole compounds as anticancer agents

  摘要：

  A series of bisintercalating DNA binding bisanthrapyrazole compounds containing piperazine linkers were designed by molecular modeling and docking techniques. Because the anthrapyrazoles are not quinones they are unable to be reductively activated like doxorubicin and other anthracyclines and thus they should not be cardiotoxic. The concentration dependent increase in DNA melting temperature was used to determine the strength of DNA binding and the bisintercalation potential of the compounds. Compounds with more than a three-carbon linker that could span four DNA base pairs achieved bisintercalation. All of the bisanthrapyrazoles inhibited human erythroleukemic K562 cell growth in the low to submicromolar concentration range. They also strongly inhibited the decatenation activity of topoisomerase II alpha and the relaxation activity of topoisomerase I. However, as measured by their ability to induce double strand breaks in plasmid DNA, the bisanthrapyrazole compounds did not act as topoisomerase II alpha poisons. In conclusion, a novel group of bisanthrapyrazole compounds were designed, synthesized, and biologically evaluated as potential anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.012
• 作为产物：
  描述：

  1,4-二溴-2-丁烯 、 N-Boc-哌嗪 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以80%的产率得到di-tert-butyl 4,4'-(but-2-ene-1,4-diyl)(E)-bis(piperazine-1-carboxylate)
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a novel series of bisintercalating DNA-binding piperazine-linked bisanthrapyrazole compounds as anticancer agents

  摘要：

  A series of bisintercalating DNA binding bisanthrapyrazole compounds containing piperazine linkers were designed by molecular modeling and docking techniques. Because the anthrapyrazoles are not quinones they are unable to be reductively activated like doxorubicin and other anthracyclines and thus they should not be cardiotoxic. The concentration dependent increase in DNA melting temperature was used to determine the strength of DNA binding and the bisintercalation potential of the compounds. Compounds with more than a three-carbon linker that could span four DNA base pairs achieved bisintercalation. All of the bisanthrapyrazoles inhibited human erythroleukemic K562 cell growth in the low to submicromolar concentration range. They also strongly inhibited the decatenation activity of topoisomerase II alpha and the relaxation activity of topoisomerase I. However, as measured by their ability to induce double strand breaks in plasmid DNA, the bisanthrapyrazole compounds did not act as topoisomerase II alpha poisons. In conclusion, a novel group of bisanthrapyrazole compounds were designed, synthesized, and biologically evaluated as potential anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.012