(E)-4-(3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-oxoprop-1-enyl)benzaldehyde | 1529791-34-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-4-(3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-oxoprop-1-enyl)benzaldehyde
• 英文别名: 4-[(E)-3-(9,10-dioxoanthracen-1-yl)-3-oxoprop-1-enyl]benzaldehyde
• CAS: 1529791-34-1
• 化学式: C₂₄H₁₄O₄
• 分子量: 366.373
• InChiKey: YFRNKLOMSPSYSN-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  邻硝基苯乙酮 、 (E)-4-(3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-oxoprop-1-enyl)benzaldehyde 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以60%的产率得到1-((2E)-3-(4-((E)-3-(2-nitrophenyl)-3-oxoprop-1-enyl)phenyl)acryloyl)anthracene-9,10-dione
  参考文献：
  名称：

  蒽醌-查尔酮杂化物：合成，初步抗增殖评估和DNA相互作用研究

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2014.10.055
• 作为产物：
  描述：

  蒽 在 盐酸 、 aluminum (III) chloride 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.08h， 生成 (E)-4-(3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-oxoprop-1-enyl)benzaldehyde
  参考文献：
  名称：

  Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.11.075

文献信息

• 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.
• 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。