1-<<2-<(tert-butoxycarbonyl)amino>ethyl>amino>-4-hydroxy-9,10-anthracenedione | 131042-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-<<2-<(tert-butoxycarbonyl)amino>ethyl>amino>-4-hydroxy-9,10-anthracenedione
• 英文别名: 1-<(Boc-aminoethyl)amino>-4-hydroxy-anthracene-9,10-dione；tert-butyl N-[2-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]ethyl]carbamate
• CAS: 131042-08-5
• 化学式: C₂₁H₂₂N₂O₅
• 分子量: 382.416
• InChiKey: JVKCLRLQKDTYCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104.73
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-<<2-<(tert-butoxycarbonyl)amino>ethyl>amino>-4-hydroxy-9,10-anthracenedione 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-(2-Amino-ethylamino)-4-hydroxy-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：

  N-叔丁氧羰基-1,2-乙二胺 、 2,3-二氢-1,4-二羟基蒽醌 在 氧气 作用下， 以55%的产率得到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：

  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

文献信息

• Synthesis, peroxidating ability, and antineoplastic evaluation of 1-[(aminoalkyl)amino]-4-hydroxy-10-imino-9-anthracenones
  作者：Maria Dzieduszycka、Sante Martelli、Jolanta Tarasiuk、Jolanta Paradziej-Lukowicz、Edward Borowski

  DOI：10.1021/jm00106a009

  日期：1991.2

  A novel group of cytotoxic anthraquinone derivatives, 1-[(aminoalkyl)amino]-4-hydroxy-10-imino-9-anthracenones, has been synthesized. It has been shown that imino analogues of the anthracenediones exhibit diminished ability to generate oxygen radicals. The cytotoxic activity of iminoanthracenones obtained was lower than that of the related quinone carbonyl analogues. One of the obtained imino compounds

  合成了一组新的细胞毒性蒽醌衍生物1-[（（氨基烷基）氨基] -4-羟基-10-亚氨基-9-蒽酮。已经表明，蒽二酮的亚氨基类似物表现出降低产生氧自由基的能力。获得的亚氨基蒽酮的细胞毒性活性低于相关的醌羰基类似物的细胞毒性活性。所获得的亚氨基化合物之一在体内显示出中等的抗白血病活性。
• DZIEDUSZYCKA, MARIA;MARTELLI, SANTE;TARASIUK, JOLANTA;PARADZIEJ-LUKOWICZ,+, J. MED. CHEM., 34,(1991) N, C. 541-546
  作者：DZIEDUSZYCKA, MARIA、MARTELLI, SANTE、TARASIUK, JOLANTA、PARADZIEJ-LUKOWICZ,+

  DOI：——

  日期：——