di-tert-butyl (((9,10-dioxo-9,10-dihydroanthracene-1,4-diyl)bis(azanediyl))bis(ethane-2,1-diyl))dicarbamate | 182931-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: di-tert-butyl (((9,10-dioxo-9,10-dihydroanthracene-1,4-diyl)bis(azanediyl))bis(ethane-2,1-diyl))dicarbamate
• 英文别名: {2-[4-(2-tert-Butoxycarbonylamino-ethylamino)-9,10-dioxo-9,10-dihydro-anthracen-1-ylamino]-ethyl}-carbamic acid tert-butyl ester
• CAS: 182931-36-8
• 化学式: C₂₈H₃₆N₄O₆
• 分子量: 524.617
• InChiKey: LZJSWXMEXYVLRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  134.86
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (((9,10-dioxo-9,10-dihydroanthracene-1,4-diyl)bis(azanediyl))bis(ethane-2,1-diyl))dicarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以100%的产率得到1,4-Bis-(2-amino-ethylamino)-anthraquinone; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Salen-anthraquinone Conjugates. Synthesis, DNA-binding and cleaving properties, effects on topoisomerases and cytotoxicity

  摘要：

  A series of amidoethylamino-anthraquinone derivatives bearing either one or two salen (bis(salicylidene)ethylenediamine) moieties complexed with Cu-II or Ni-II have been synthesized, and their DNA-binding and cleaving properties examined. The effects of the mono- and di-substituted anthracenedione-salen conjugates on DNA cleavage mediated by topoisomerases I and II have also been determined, as well as their cytotoxicity toward human KB cells. The anthraquinone-salen . Ni-II conjugates bind to CC-rich sequences in DNA, but do not cleave the macromolecule. By contrast, the anthraquinone-salen . Cu-II hybrids do not recognize particular nucleotide sequences but efficiently induce single-strand breaks in DNA after activation. The 5,8-dihydroxy-anthraquinone conjugates are more cytotoxic and more potent toward topoisomerase II than the non-hydroxylated analogues, but they are less cytotoxic than the salen-free anthraquinones. The attachment of a salen . Cu-II complex to the anthra quinone chromophore can confer DNA cleaving properties in vitro, but this is at the expense of cytotoxic activity. Anthraquinone-salen . Cu-II complexes may find useful employ as footprinting probes for investigating ligand-DNA interactions. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00082-x
• 作为产物：
  描述：

  在 air 作用下， 以 甲醇 为溶剂， 生成 di-tert-butyl (((9,10-dioxo-9,10-dihydroanthracene-1,4-diyl)bis(azanediyl))bis(ethane-2,1-diyl))dicarbamate
  参考文献：
  名称：

  Synthesis, DNA binding, and cytotoxicity of 1,4-bis(2-amino-ethylamino)anthraquinone–amino acid conjugates

  摘要：

  Two series of 1,4-bis(2-amino-ethylamino)anthraquinone-amino acid conjugates (BACs), ametantrone (AT)-amino acid conjugates (AACs) and mitoxantrone (MX)-amino acid conjugates (MACs), were designed and synthesized. The DNA binding of BACs was evaluated by DNA thermal denaturation experiment. In the series, the methionine-substituted BACs had the weakest DNA binding, while the lysine-substituted BACs had the highest T-m values. The abilities of BACs to inhibit the growth of MCF-7, NCI-H460, SF-268, and PC-3 cell lines were determined. L-Met-MAC 16 and L-Lys-MAC 20 were the most potent growth inhibitors. MAC 16 was more cytotoxic than MX, whereas the T-m of MAC 16 was much lower than that of MX In contrast to MAC 16, L-Lys-MAC 20 demonstrated higher T-m than MX. These data suggested that Met-BACs possessed a different pharmacological profile, in which the ability to stabilize DNA is not parallel to the ability to kill cancer cells, from that of AT and MX. The primary mechanism of cytotoxicity for MAC 16 was most likely through TOP2 poisoning. Therefore, MAC 16 may provide a lead for the development of novel generations of anthraquinone-type antitumor agents. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.012