2-(2-hydroxyethyl)amino-3-methylnaphthoquinone | 55464-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-hydroxyethyl)amino-3-methylnaphthoquinone
• 英文别名: 2-Methyl-3<2-hydroxyethylamino->-1,4-naphthochinon；2-(2-Hydroxyethylamino)-3-methylnaphthalene-1,4-dione
• CAS: 55464-53-4
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: IKXJMZTUOAVWRA-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C
• 沸点：
  425.6±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethyl)amino-3-methylnaphthoquinone 、 2,4-di(α-methoxyethyl)deuteroporphyrin IX 在 吡啶 、 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以71.7%的产率得到
  参考文献：
  名称：

  Synthesis and study of the spectral properties of diquinone derivatives of hematoporphyrin IX

  摘要：

  DOI：

  10.1007/bf00486797
• 作为产物：
  描述：

  甲萘醌 、 C.I.酸性橙108 以25%的产率得到2-(2-hydroxyethyl)amino-3-methylnaphthoquinone
  参考文献：
  名称：

  Evstigneeva, R. P.; Borovkov, V. V.; Filippovich, E. I., Doklady Chemistry, 1987, vol. 293, p. 186 - 188

  摘要：

  DOI：

文献信息

• Synthesis and Properties of Pheophorbide-Quinone Compounds
  作者：Victor V. Borovkov、Alexander A. Gribkov、Andrei N. Kozyrev、Alexander S. Brandis、Akito Ishida、Yoshiteru Sakata

  DOI：10.1246/bcsj.65.1533

  日期：1992.6

  New pheophorbide-quinone derivatives with a different kind of quinone moieties were synthesized by mixed anhydride method. The structures of these compounds were confirmed by UV, IR, 1H NMR, fluorescence, and mass spectra. Effective fluorescence quenching of the pheophorbide chromophores in the synthesized molecules was observed depending on the electron-accepting properties of the quinone fragment and spatial disposition of the donor and acceptor. Electron-transfer rate constants were calculated based on fluorescence decay measurements. The role of energetic and conformational changes of pheophorbide-quinones in the electron-transfer processes is discussed.

  通过混合酸酐法合成了具有不同醌基的新型叶绿素醌衍生物。通过紫外、红外、1H核磁共振、荧光和质谱对这些化合物的结构进行了确认。根据醌基的受电子性质以及供体和受体的空间分布，观察到了合成分子中叶绿素醌基的有效荧光猝灭。根据荧光衰减测量计算了电子转移速率常数。讨论了叶绿素醌在电子转移过程中的能量和构象变化的作用。
• Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity
  作者：Marie-Priscille Brun、Emmanuelle Braud、Delphine Angotti、Odile Mondésert、Muriel Quaranta、Matthieu Montes、Maria Miteva、Nohad Gresh、Bernard Ducommun、Christiane Garbay

  DOI：10.1016/j.bmc.2005.05.005

  日期：2005.8

  CDC25 dual-specificity phosphatases are essential key regulators of eukaryotic cell cycle progression and the CDC25A and B isoforms are over-expressed in different tumors and related cancer cell lines. CDC25s are now considered to be interesting targets in the search for novel anticancer agents. We describe new compounds derived from vitamin K-3 that inhibit CDC25B activity with IC50 values in the low micromolar range. These naphthoquinone derivatives also display antiproliferative activity on HeLa cells as expected for CDC25 inhibitors and inhibit cell growth in a clonogenic assay at submicromolar concentrations. They increase inhibitory tyrosine 15 phosphorylation of CDK and induce the cleavage of PARP, a hallmark of apoptosis. (c) 2005 Elsevier Ltd. All rights reserved.
• Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases
  作者：Shugeng Cao、Brian T. Murphy、Caleb Foster、John S. Lazo、David G.I. Kingston

  DOI：10.1016/j.bmc.2008.10.090

  日期：2009.3

  Some simplified adociaquinone B analogs and a series of 1,4-naphthoquinone derivatives were synthesized and tested against the three enzymes Cdc25B, MKP-1, and MKP-3. Cdc25B and MKP-1 in particular are enzymes overexpressed in human cancer cells, and they represent potential molecular targets for novel cancer chemotherapeutic treatments. A number of analogs exhibited significant inhibitory activity against these enzymes, and the bioassay data in addition to structure-activity relationships of these compounds will be discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and spectral properties of porphyrinquinone derivatives based on deuteroporphyrin IX
  作者：V. V. Borovkov、E. I. Filippovich、R. P. Evstigneeva

  DOI：10.1007/bf00755687

  日期：1988.5
• BOROVKOV, V. V.;FILIPPOVICH, E. I.;EVSTIGNEEVA, R. P., XIMIYA GETEROTSIKL. SOED.,(1988) N 5, 608-616
  作者：BOROVKOV, V. V.、FILIPPOVICH, E. I.、EVSTIGNEEVA, R. P.

  DOI：——

  日期：——