1,5-bis-(2-morpholin-4-yl-ethylamino)-anthraquinone | 3248-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,5-bis-(2-morpholin-4-yl-ethylamino)-anthraquinone
• 英文别名: 1,5-Bis(2-morpholin-4-ylethylamino)anthracene-9,10-dione
• CAS: 3248-30-4
• 化学式: C₂₆H₃₂N₄O₄
• 分子量: 464.564
• InChiKey: LHMWSQJNABDMTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 、 1,5-二氯蒽醌 以 neat (no solvent) 为溶剂， 以85%的产率得到1,5-bis-(2-morpholin-4-yl-ethylamino)-anthraquinone
  参考文献：
  名称：

  Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones

  摘要：

  Structural features from the anticancer prodrug nemorubicin (MMDX) and the DNA-binding molecule DRAQ5(TM) were used to prepare anthraquinone-based compounds, which were assessed for their potential to interrogate cytochrome P450 (CYP) functional activity and localisation. 1,4-disubstituted anthraquinone 8 was shown to be 5-fold more potent in EJ138 bladder cancer cells after CYP1A2 bioactivation. In contrast, 1,5-bis((2-morpholinoethyl)amino) substituted anthraquinone 10 was not CYP-bioactivated but was shown to be fluorescent and subsequently photo-activated by a light pulse (at a bandwidth 532-587 nm), resulting in punctuated foci accumulation in the cytoplasm. It also showed low toxicity in human osteosarcoma cells. These combined properties provide an interesting prospective approach for opto-tagging single or a sub-population of cells and seeking their location without the need for continuous monitoring. Crown Copyright (C) 2018 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.03.040

文献信息

• Synthesis of aminoanthraquinone derivatives and their in vitro evaluation as potential anti-cancer drugs
  作者：J KATZHENDLER、K GEAN、G BARAD、Z TASHMA、R BENSHOSHAN、I RINGEL、U BACHRACH、A RAMU

  DOI：10.1016/0223-5234(89)90159-1

  日期：1989.1
• KATZHENDLER, JEHOSHUA;GEAN, KERIA-FIORELLA;BAR-AD, GIDON;TASHMA, ZEEV;BEN+, EUR. J. MED. CHEM., 24,(1989) N, C. 23-30
  作者：KATZHENDLER, JEHOSHUA、GEAN, KERIA-FIORELLA、BAR-AD, GIDON、TASHMA, ZEEV、BEN+

  DOI：——

  日期：——
• A COLORANT COMPOSITION, A POLYMER NANOCOMPOSITE COMPRISING THE COLORANT COMPOSITION AND ARTICLES PRODUCED THEREFROM
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP1147147A1

  公开（公告）日：2001-10-24
• USE OF ANTHRAQUINONE DYES AND OF FLUORESCENT DYES FOR DYEING KERATIN FIBRES, DYEING PROCESS AND COMPOSITION
  申请人：L'Oréal

  公开号：EP3558235B1

  公开（公告）日：2021-09-08
• US6486254B1
  申请人：——

  公开号：US6486254B1

  公开（公告）日：2002-11-26