7,8-methylenedioxy-4'-methoxyflavanone | 1232362-76-3

• 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: 7,8-methylenedioxy-4'-methoxyflavanone
• 英文别名: 8-(4-Methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-h]chromen-6-one
• CAS: 1232362-76-3
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: DNSNRCPRKDOGRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7,8-methylenedioxy-4'-methoxyflavanone 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 生成 7,8-methylendioxy-4'-methoxyflavone
  参考文献：
  名称：

  Methylenedioxy flavonoids: Assessment of cytotoxic and anti-cancer potential in human leukemia cells

  摘要：

  A new series of chalcones, flavanones and flavones with methylenedioxy group at the 3',4' position in chalcone, 7,8 position in flavanones and flavones with mono-, di- and trimethoxy groups in the benzaldehyde ring have been assessed for their effect on proliferation, cytotoxic potential and apoptosis in human leukemia cells. Among the tested compounds, the chalcone series showed the best activity and chalcone 3 (mono methoxy group at the ortho position in A-ring) showed a significant effect on down-regulation of cancer cell proliferation and viability in three different leukemia cell lines (K562, Jurkat, U937). The executioner caspase cleavage analyses indicated that the cytotoxic effect mediated by chalcone 3 is due to induction of apoptotic cell death. Interestingly, the cytotoxic effect was cell type-specific and targeted preferentially cancer cells as peripheral blood mononuclear cells (PBMCs) from healthy donors were less affected by the treatment compared to K562, Jurkat and U937 leukemia cells. Altogether our results indicate a potential drug candidate with interesting differential toxicity obeying Lipinski's rule of five.

  DOI：

  10.1016/j.ejmech.2014.07.003
• 作为产物：
  描述：

  2'-hydroxy-3',4'-(methylenedioxy)acetophenone 在 三氟乙酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 7,8-methylenedioxy-4'-methoxyflavanone
  参考文献：
  名称：

  亚甲二氧基查耳酮，黄烷酮和黄酮的电喷雾串联质谱分析。

  摘要：

  理由数种被单，二和三甲氧基取代的亚甲二氧基查耳酮，黄烷酮和黄酮已用于治疗增生性疾病，例如癌症和炎性疾病。这些类黄酮在生物学中的应用需要一种分析方法，以确保药物代谢后对其结构的详细了解。方法使用Q-TOF 2仪器获得电喷雾电离质谱（ESI-MS）和串联质谱（ESI-MS / MS）光谱。使用标准的分离和激发程序（激活q值为0.25，激活时间为30 ms），通过在LXQ线性离子阱质谱仪中获得的CID-MS（2-3）谱图分析了碎片模式及其途径。ESI-MS和ESI-MS（n）条件：喷雾电压5 kV，氮气8.00鞘气流速（任意），加热的毛细管温度275°C，毛细管电压10.99 V; 镜筒透镜电压为75.01V。结果查耳酮的ESI-MS / MS谱图与其相应的异构黄烷酮具有（0，α）A（+）/（1,3）A（+）和（0,1' ）B（+）/（1,4）B（+）裂解。其他常见的损失包括（•）CH3，H2O

  DOI：

  10.1002/rcm.6577

文献信息

• Electrospray tandem mass spectrometry analysis of methylenedioxy chalcones, flavanones and flavones
  作者：José C. J. M. D. S. Menezes、José A. S. Cavaleiro、Shrivallabh P. Kamat、Cristina M. R. F. Barros、M. Rosário M. Domingues

  DOI：10.1002/rcm.6577

  日期：2013.6.30

  tandem mass (ESI-MS/MS) spectra were acquired using a Q-TOF 2 instrument. Fragmentation patterns and their pathways were analyzed by CID-MS(2-3) spectra acquired in a LXQ linear ion trap mass spectrometer using standard isolation and excitation procedures (activation q value of 0.25, activation time of 30 ms). ESI-MS and ESI-MS(n) conditions: spray voltage 5 kV, nitrogen 8.00 sheath gas flow rate (arb)

  理由数种被单，二和三甲氧基取代的亚甲二氧基查耳酮，黄烷酮和黄酮已用于治疗增生性疾病，例如癌症和炎性疾病。这些类黄酮在生物学中的应用需要一种分析方法，以确保药物代谢后对其结构的详细了解。方法使用Q-TOF 2仪器获得电喷雾电离质谱（ESI-MS）和串联质谱（ESI-MS / MS）光谱。使用标准的分离和激发程序（激活q值为0.25，激活时间为30 ms），通过在LXQ线性离子阱质谱仪中获得的CID-MS（2-3）谱图分析了碎片模式及其途径。ESI-MS和ESI-MS（n）条件：喷雾电压5 kV，氮气8.00鞘气流速（任意），加热的毛细管温度275°C，毛细管电压10.99 V; 镜筒透镜电压为75.01V。结果查耳酮的ESI-MS / MS谱图与其相应的异构黄烷酮具有（0，α）A（+）/（1,3）A（+）和（0,1' ）B（+）/（1,4）B（+）裂解。其他常见的损失包括（•）CH3，H2O
• Synthesis of 7,8-Methylenedioxy-4′-Methoxyisoflavone from Indigofera Linnaei and Two New Related Flavonoids
  作者：Jose C.J.M.D.S. Menezes、Janardan K. Kirtany、Shrivallabh P. Kamat

  DOI：10.3184/030823409x12613944078394

  日期：2010.1

  The synthesis of naturally occurring 7,8-methylenedioxy-4′-methoxyisoflavone and 7,8-methylenedioxy-4′-methoxy-flavone from 2′-hydroxy-3′,4′-methylenedioxy-4-methoxychalcone via the intermediacy of 7,8-methylenedioxy-4′-methoxyflavanone using thallium(III) acetate and catalytic amount of perchloric acid is reported. The products flavanone and the flavone are new flavonoids characterised by spectral analysis.

  以 2′-羟基-3′-4′-亚甲二氧基-4′-甲氧基异黄酮和 7,8-亚甲二氧基-4′-甲氧基黄酮为中间体，利用铊（III）乙酸酯和梓桐合成天然的 7,8-亚甲二氧基-4′-甲氧基黄酮、报告使用乙酸铊（III）和催化量的高氯酸，通过 7,8-亚甲二氧基-4′-甲氧基黄烷酮的中间体，从 2′-羟基-3′, 4′-亚甲二氧基-4-甲氧基查尔酮制备出黄烷酮和黄酮。通过光谱分析，产物黄烷酮和黄酮是新的黄酮类化合物。
• Methylenedioxy flavonoids: Assessment of cytotoxic and anti-cancer potential in human leukemia cells
  作者：Barbora Orlikova、José C.J.M.D.S. Menezes、Seungwon Ji、Shrivallabh P. Kamat、José A.S. Cavaleiro、Marc Diederich

  DOI：10.1016/j.ejmech.2014.07.003

  日期：2014.9

  A new series of chalcones, flavanones and flavones with methylenedioxy group at the 3',4' position in chalcone, 7,8 position in flavanones and flavones with mono-, di- and trimethoxy groups in the benzaldehyde ring have been assessed for their effect on proliferation, cytotoxic potential and apoptosis in human leukemia cells. Among the tested compounds, the chalcone series showed the best activity and chalcone 3 (mono methoxy group at the ortho position in A-ring) showed a significant effect on down-regulation of cancer cell proliferation and viability in three different leukemia cell lines (K562, Jurkat, U937). The executioner caspase cleavage analyses indicated that the cytotoxic effect mediated by chalcone 3 is due to induction of apoptotic cell death. Interestingly, the cytotoxic effect was cell type-specific and targeted preferentially cancer cells as peripheral blood mononuclear cells (PBMCs) from healthy donors were less affected by the treatment compared to K562, Jurkat and U937 leukemia cells. Altogether our results indicate a potential drug candidate with interesting differential toxicity obeying Lipinski's rule of five.