1,4-bis-[(2-aminoethyl)amino]-5,8-dihydroxyanthraquinone | 96555-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-bis-[(2-aminoethyl)amino]-5,8-dihydroxyanthraquinone
• 英文别名: 1,4-bis(2-aminoethylamino)-5,8-dihydroxyanthracene-9,10-dione；1,4-bis[(2-aminoethyl)amino]-5,8-dihydroxy-9,10-anthracenedione；1,4-bis[(2-aminoethyl)-amino]-5,8-dihydroxyanthraquinone base；base 1,4-bis[(2-aminoethyl)amino]-5,8-dihydroxyanthraquinone；1,4-bis[(2-aminoethyl)-amino]-5,8-dihydroxyanthraquinone；1,4-bis[(2-aminoethyl)amino]-5,8-dihydroxyanthraquinone；1,4-Bis((2-aminoethyl)amino)-5,8-dihydroxy-9,10-anthraquinone
• CAS: 96555-65-6
• 化学式: C₁₈H₂₀N₄O₄
• 分子量: 356.381
• InChiKey: CLVFWRBVFBUDQU-UHFFFAOYSA-N

物化性质

• 沸点：
  722.6±60.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  151
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4-bis-[(2-aminoethyl)amino]-5,8-dihydroxyanthraquinone 在 苯甲醛 作用下， 以 甲苯 为溶剂， 生成 1,4-dihydroxy-5,8-bis[[2-[(phenylmethylene)amino]ethyl]amino]-9,10-anthracenedione
  参考文献：
  名称：

  Schiff bases of [(aminoalkyl or substituted

  摘要：

  本公开说明了一种新的席夫碱，其为1,4-双[(ω-氨基烷基)氨基]-9,10-蒽醌和其还原型的亚甲基基团，可用作螯合剂，并用于诱导哺乳动物的白血病退化和/或抑制肿瘤生长。

  公开号：

  US04540788A1
• 作为产物：
  描述：

  1,4-bis[Boc-aminoethylamino]-5,8-dihydroxyanthracene-9,10-dione 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1,4-bis-[(2-aminoethyl)amino]-5,8-dihydroxyanthraquinone
  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

• Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from <i>N</i>-Fmoc-Protected α-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library
  作者：Ying-Ying Chen、Li-Te Chang、Hung-Wei Chen、Chia-Ying Yang、Ling-Wei Hsin

  DOI：10.1021/acscombsci.6b00160

  日期：2017.3.13

  A fast and facile synthesis of a series of 4-nitrophenyl 2-azidoethylcarbamate derivatives as activated urea building blocks was developed. The N-Fmoc-protected 2-aminoethyl mesylates derived from various commercially available N-Fmoc-protected α-amino acids, including those having functionalized side chains with acid-labile protective groups, were directly transformed into 4-nitrophenyl 2-azidoethylcarbamate

  快速，简便地合成了一系列4-硝基苯基2-叠氮基乙基氨基甲酸酯衍生物作为活化尿素的基础。衍生自各种市售N -Fmoc保护的α-氨基酸的N -Fmoc保护的2-氨基乙基甲磺酸酯，包括那些具有带有酸不稳定保护基的官能化侧链的氨基酸，直接转化为4-硝基苯基2-叠氮基乙基氨基甲酸酯衍生物。通过一锅两步反应1 h。这些尿素结构单元用于制备一系列含尿素部分的米托蒽醌-氨基酸共轭物，产率为75-92％，尿素化合物文库的平行溶液相合成由30个成员组成，总产率为38-70％ 。
• New Anthracenedione Derivatives with Improved Biological Activity by Virtue of Stable Drug−DNA Adduct Formation
  作者：Oula C. Mansour、Benny J. Evison、Brad E. Sleebs、Keith G. Watson、Abraham Nudelman、Ada Rephaeli、Damian P. Buck、J. Grant Collins、Rebecca A. Bilardi、Don R. Phillips、Suzanne M. Cutts

  DOI：10.1021/jm901894c

  日期：2010.10.14

  on the opposite DNA strand. New derivatives based on the pixantrone and mitoxantrone backbones were synthesized, and these incorporated primary amino groups as well as extended side chains. The stability of DNA adducts increased with increasing side chain length of the derivatives. A mitoxantrone derivative bearing extended side chains (7) formed the most stable adducts with ∼100-fold enhanced stability

  米托蒽醌是一种抗癌剂，可作为拓扑异构酶II毒药，但是，它也可以被甲醛激活以形成DNA加合物。Pixantrone是一种2-氮杂-蒽二酮，其侧链具有末端伯氨基，与米托蒽醌相比，能更有效地与DNA形成甲醛介导的加合物。分子模型研究表明，蒽二酮侧臂“连接子”区域的延伸将使末端伯氨基具有更大的柔韧性，从而可进入相对DNA链上的鸟嘌呤残基。合成了基于pixantrone和mitoxantrone主链的新衍生物，这些衍生物结合了伯氨基和延伸的侧链。DNA加合物的稳定性随衍生物侧链长度的增加而增加。7）与米托蒽醌相比，形成了最稳定的加合物，稳定性提高了约100倍。这一发现非常令人感兴趣，因为预期寿命长的药物-DNA加合物会在细胞周期的所有阶段扰乱DNA依赖性功能。
• Cytotoxic N,N'-bis (succinyl-peptide-) derivatives of 1,4-bis (aminoalkyl)-5,8-dihydroxyanthraquinones and antibody conjugates thereof
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0489220A1

  公开（公告）日：1992-06-10

  The present invention is concerned with novel N,N'-bis(succinyl-peptide)-derivatives of 1,4-bis(aminoalkyl)-5,8-dihydroxyanthraquinones and the corresponding antibody conjugates thereof each of which have potential use in the treatment of human carcinomas.

  本发明涉及1,4-双(氨基烷基)-5,8-二羟基蒽醌的新型N,N'-双(琥珀酰肽)衍生物及其相应的抗体偶联物，它们都具有在人类癌症治疗中的潜在用途。
• Novel Schiff bases of (aminoalkyl or substituted aminoalkyl)-amino-9,10-anthracenediones
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0131787A2

  公开（公告）日：1985-01-23

  This disclosure describes novel Schiff bases of 1,4- bis[(ω-aminoalkyl)amino]-9, 10-anthracenediones and leuco bases thereof which are useful as chelating agents and for inducing regression of leukemia and/or inhibiting tumor growth in mammals.

  本公开描述了 1，4-双[(ω-氨基烷基)氨基]-9，10-蒽二酮的新型希夫碱及其白基，它们可用作螯合剂，并可诱导哺乳动物体内白血病的消退和/或抑制肿瘤的生长。
• Use of 1,4 bis(substituted) anthrachinones for the manufacture of immunosuppresiva
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0154117A1

  公开（公告）日：1985-09-11

  This disclosure describes a method of inducing immunosuppression in mammals by the parenteral administration of certain 1,4 bis(substituted anthraquinones.

  本公开描述了一种通过肠外给药某些 1,4-双（取代蒽醌）诱导哺乳动物免疫抑制的方法。