1,4-bis[Boc-aminoethylamino]-5,8-dihydroxyanthracene-9,10-dione | 149792-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-bis[Boc-aminoethylamino]-5,8-dihydroxyanthracene-9,10-dione
• 英文别名: tert-butyl N-[2-[[5,8-dihydroxy-4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]-9,10-dioxoanthracen-1-yl]amino]ethyl]carbamate
• CAS: 149792-11-0
• 化学式: C₂₈H₃₆N₄O₈
• 分子量: 556.616
• InChiKey: QXAPWBSQPHOPLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  40.0
• 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：
  175.32
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,4-bis[Boc-aminoethylamino]-5,8-dihydroxyanthracene-9,10-dione 在 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 tert-butyl N-[2-[2-[[5,8-dihydroxy-4-[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]ethylamino]-9,10-dioxoanthracen-1-yl]amino]ethylamino]-2-oxoethyl]carbamate
  参考文献：
  名称：

  New Peptidyl-Anthraquinones: Synthesis and DNA Binding

  摘要：

  Aminoacyl- hydroxy-anthraquinones bearing glicyl, valyl, lysyl and tryptophanyl residues in the side-chain were synthesized as new potential DNA-directed drugs. These compounds bind very tightly to double-stranded DNA by intercalating their planar portion into the nucleic acid and further stabilizing the complex through electrostatic contacts with the backbone phosphates. All protonated groups in the side-chains participate in the latter process. The free energy of DNA-binding corrected for the electrostatic contribution is similar for the lysyl and glicyl derivatives, which points to a common geometry of intercalation.

  DOI：

  10.1080/07328319808004756
• 作为产物：
  描述：

  在 air 作用下， 以 甲醇 为溶剂， 生成 1,4-bis[Boc-aminoethylamino]-5,8-dihydroxyanthracene-9,10-dione
  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

文献信息

• LANTHANIDE COMPLEXES BASED ON TRIETHYLENETETRAMINE-N,N,N',N'',N''',N'''-HEXAACETIC ACID DERIVATIVES
  申请人：UNIVERSITE D'ORLEANS

  公开号：US20190330242A1

  公开（公告）日：2019-10-31

  The present invention relates to a complex comprising at least one lanthanide (Ln) and at least one compound (C) comprising a unit of formula (I) below: said unit of formula (I) being covalently connected to at least one antenna which absorbs at a wavelength ranging from 500 nm to 900 nm.

  本发明涉及一种复合物，包括至少一种镧系元素（Ln）和至少一种化合物（C），所述化合物（C）包含下面的式（I）单元：所述式（I）单元与至少一个在波长范围为500纳米至900纳米吸收的天线共价连接。
• Salen-anthraquinone Conjugates. Synthesis, DNA-binding and cleaving properties, effects on topoisomerases and cytotoxicity
  作者：Sylvain Routier、Nicole Cotelle、Jean-Pierre Catteau、Jean-Luc Bernier、Michael J. Waring、Jean-François Riou、Christian Bailly

  DOI：10.1016/0968-0896(96)00082-x

  日期：1996.8

  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
• Synthesis and antitumor properties of an anthraquinone bisubstituted by the copper chelating peptide Gly-Gly-L-His
  作者：Elisabeth Morier-Teissier、Nezha Boitte、Nicole Helbecque、Jean Luc Bernier、Nicole Pommery、Jean Loup Duvalet、Charles Fournier、Bernard Hecquet、Jean Pierre Catteau、Jean Pierre Henichart

  DOI：10.1021/jm00067a005

  日期：1993.7

  A new molecule 4 [(GGH-DAE)2DHQ] associating the 1,4,5,8-tetrahydroxyanthraquinone ring (DHQ) of the antitumor drug mitoxantrone (2), two diaminoethylene chains (DAE), and the metal-chelating peptide Gly-Gly-His (GGH) has been synthesized. Such a molecule presents characteristics able to induce antitumor activity: compound 4 intercalates into DNA as measured by DELTAT(m), fluorescence quenching, and viscometry; ESR studies demonstrate that several types of Cu complexes are formed depending on PH; and the production of free radicals, as evidenced by spin-trapping, is enhanced by 4. In vitro, in leukemia cells L1210 and mammary cells MCF7, 4 is slightly less cytostatic than mitoxantrone, but substantially less toxic. In vivo, in leukemia P388 on mice, a T/C value of 230 is obtained at 25 mg/kg, higher than the one of mitoxantrone, which is toxic at the same dose.