1-乙酰基蒽-9,10-二酮 | 53336-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-乙酰基蒽-9,10-二酮
• 英文名称: 1-acetylanthraquinone
• 英文别名: 1-Acetyl-anthrachinon；1-Acetylanthracene-9,10-dione
• CAS: 53336-60-0
• 化学式: C₁₆H₁₀O₃
• 分子量: 250.254
• InChiKey: VONYRERAAKXLRY-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  458.7±34.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰基蒽-9,10-二酮 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 生成 1-vinyl-anthraquinone
  参考文献：
  名称：

  Manecke,G.; Storck,W., Chemische Berichte, 1961, vol. 94, p. 3239 - 3250

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-dimethyl-benz[de]anthracen-7-one 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 1-乙酰基蒽-9,10-二酮
  参考文献：
  名称：

  Alpha-anthraquinonyl ketones and process of preparing same

  摘要：

  公开号：

  US01725927A1

文献信息

• Anthraquinone–chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies
  作者：Violeta Marković、Nevena Debeljak、Tatjana Stanojković、Branka Kolundžija、Dušan Sladić、Miroslava Vujčić、Barbara Janović、Nikola Tanić、Milka Perović、Vesna Tešić、Jadranka Antić、Milan D. Joksović

  DOI：10.1016/j.ejmech.2014.10.055

  日期：2015.1

  Novel anthraquinone based chalcone compounds were synthesized starting from 1-acetylanthraquinone in a Claisen–Schmidt reaction and evaluated for their anticancer potential against three human cancer cell lines. Compounds 4a, 4b and 4j showed promising activity in inhibition of HeLa cells with IC50 values ranging from 2.36 to 2.73 μM and low cytotoxicity against healthy MRC-5 cell lines. The effects

  从新的蒽醌类查尔酮化合物开始，在Claisen-Schmidt反应中从1-乙酰基蒽醌开始合成，并评估了它们对三种人类癌细胞系的抗癌潜力。化合物4a，4b和4j在抑制HeLa细胞方面表现出有希望的活性，IC 50值为2.36至2.73μM，并且对健康MRC-5细胞系的细胞毒性较低。通过流式细胞术研究了化合物对细胞周期的影响。发现4a，4b和4j引起细胞在S和G2 / M期的蓄积，并呈剂量依赖性，并诱导caspase依赖性凋亡。这三种化合物都具有小牛胸腺DNA结合活性。所确定的通过吸收滴定（2.65×10结合常数3 中号-1，1.36×10 3 中号-1和2.51×10 3 中号-1的图4a / CT-DNA，4B / CT-DNA和4J / CT-DNA，分别）和荧光位移分析将4a，4b和4j指定为强小沟结合剂，但未观察到质粒DNA的切割。
• Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity
  作者：Branka Kolundžija、Violeta Marković、Tatjana Stanojković、Ljubinka Joksović、Ivana Matić、Nina Todorović、Marijana Nikolić、Milan D. Joksović

  DOI：10.1016/j.bmcl.2013.11.075

  日期：2014.1

  A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino group showed potent activity against all target cells with IC50 values ranging from 1.76 to 6.11 mu M. A mode of action study suggested that compounds induced changes typical for apoptosis in HeLa cells. The most active compounds inhibited tubulogenesis and 5h was found to exhibit a strong anti-angiogenic effect. (C) 2013 Elsevier Ltd. All rights reserved.
• Bassilios,H.F. et al., Recueil des Travaux Chimiques des Pays-Bas, 1963, vol. 82, p. 298 - 301
  作者：Bassilios,H.F. et al.

  DOI：——

  日期：——
• Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone–thiosemicarbazones with tautomerizable methylene group
  作者：Violeta Marković、Ana Janićijević、Tatjana Stanojković、Branka Kolundžija、Dušan Sladić、Miroslava Vujčić、Barbara Janović、Ljubinka Joksović、Predrag T. Djurdjević、Nina Todorović、Snežana Trifunović、Milan D. Joksović

  DOI：10.1016/j.ejmech.2013.03.071

  日期：2013.6

  A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents
  作者：Tatjana Stanojković、Violeta Marković、Ivana Z. Matić、Milan P. Mladenović、Nina Petrović、Ana Krivokuća、Miloš Petković、Milan D. Joksović

  DOI：10.1016/j.bmcl.2018.06.048

  日期：2018.8

  A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structurebased 3-D QSAR models for 6f, 6e, 6i and 61 describe pro-apoptotic activity against caspase-3.