2-(2,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one | 58124-14-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(2,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
• 英文别名: 2-(2,4-dimethoxy-phenyl)-5,7-dihydroxy-chromen-4-one；2-(2,4-Dimethoxy-phenyl)-5,7-dihydroxy-chromen-4-on；4H-1-Benzopyran-4-one, 2-(2,4-dimethoxyphenyl)-5,7-dihydroxy-；2-(2,4-dimethoxyphenyl)-5,7-dihydroxychromen-4-one
• CAS: 58124-14-4
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: XXBKIZHPGZPESN-UHFFFAOYSA-N

物化性质

• 熔点：
  258-259 °C
• 沸点：
  558.8±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one 在 三氯化铝 、 potassium carbonate 、 丙酮 、 苯 作用下， 生成 降桂木生黄亭
  参考文献：
  名称：

  Gupta; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 611,614

  摘要：

  DOI：
• 作为产物：
  描述：

  间苯三酚 在 盐酸 、 sodium hydroxide 、 zinc(II) chloride 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 生成 2-(2,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Inhibitory effect of flavonoids on human glutaminyl cyclase

  摘要：

  Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4' (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.064

文献信息

• Regioselective synthesis and evaluation of 2-amino 3-cyano chromene-chrysin hybrids as potential anticancer agents
  作者：Hui-Juan Wang、Yan-You Zhou、Xiong-Li Liu、Wen-Hui Zhang、Shuang Chen、Xiong-Wei Liu、Ying Zhou

  DOI：10.1016/j.bmcl.2020.127087

  日期：2020.5

  The first example of Ca(OH)(2)-activated p-regioselective synthesis of chrysin-fused chromene was reported through a cascade Michael/cyclization of chrysin and arylidenemalononitrile. The newly synthesized structurally diverse 2-amino 3-cyano chromene-chrysin hybrids 3 were evaluated for their in vitro anticancer activity, and some of the compounds showed stronger anti-proliferative activity against K562, PC-3, A549 and NCI-H1299 than parent compound chrysin, and demonstrated equipotent potency compared with the reference drug of cisplatin. In particular, compound 3h had the highest cytotoxicity towards K562 cells (IC50 = 6.41 mu M). Furthermore, compound 3h induced apoptosis of K562 cells in a concentration-dependent manner, as well as induced the apoptosis possibly through promoting the formation of apoptotic DNA of cancer cell via the intrinsic apoptotic pathway. Thus, our results provide in vitro evidence that compound 3h may be a potential candidate for the development of new anti-tumour drugs.
• Design, synthesis and evaluation of structurally diverse chrysin-chromene-spirooxindole hybrids as anticancer agents
  作者：Wen-Hui Zhang、Shuang Chen、Xiong-Li Liu、Ting-Ting Feng、Wu-De Yang、Ying Zhou

  DOI：10.1016/j.bmc.2019.115109

  日期：2019.11

  A series of structurally diverse chrysin-chromene-spirooxindole hybrids were designed, synthesized via a Knoevenagel/Michael/cyclization of chrysin and isatylidene malononitrile derivatives through utilizing a hybrid pharmacophore approach. The newly synthesized compounds were evaluated for their in vitro anticancer activity, and most of the compounds showed stronger anti-proliferative activity than parent compound chrysin. In particular, compound 3e had the highest cytotoxicity towards A549 cells (IC50 = 3.15 +/- 0.51 mu M), and had better selectivity in A549 cells and normal MRC-5 cells. Furthermore, compound 3e could significantly inhibit the proliferation and migration of A549 cells in a dose-dependent manner, as well as induce the apoptosis possibly through mitochondria-mediated caspase-3/8/9 activation and multi-target co-regulation of the p53 signaling pathway. Thus, our results provide in vitro evidence that compound 3e may be a potential candidate for the development of new anti-tumour drugs.
• Robinson; Venkataraman, Journal of the Chemical Society, 1929, p. 63
  作者：Robinson、Venkataraman

  DOI：——

  日期：——
• Inhibitory effect of flavonoids on human glutaminyl cyclase
  作者：Manman Li、Yao Dong、Xi Yu、Yongdong Zou、Yizhi Zheng、Xianzhang Bu、Junmin Quan、Zhendan He、Haiqiang Wu

  DOI：10.1016/j.bmc.2016.03.064

  日期：2016.5

  Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4' (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC. (C) 2016 Elsevier Ltd. All rights reserved.
• Gupta; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 611,614
  作者：Gupta、Seshadri

  DOI：——

  日期：——