3-hydroxy-8,9,9-trimethyl-2-phenyl-8,9-dihydro-4H-furo[2,3-h]chromen-4-one | 1310461-36-9

• 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: 3-hydroxy-8,9,9-trimethyl-2-phenyl-8,9-dihydro-4H-furo[2,3-h]chromen-4-one
• 英文别名: 3-hydroxy-8,9,9-trimethyl-2-phenyl-8H-furo[2,3-h]chromen-4-one
• CAS: 1310461-36-9
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: UYCOQNOWHJTBHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-hydroxy-7-(3-methylbut-2-enyloxy)-2-phenyl-4H-chromen-4-one 以 N-甲基吡咯烷酮 为溶剂， 反应 0.75h， 以36%的产率得到3-hydroxy-8,9,9-trimethyl-2-phenyl-8,9-dihydro-4H-furo[2,3-h]chromen-4-one
  参考文献：
  名称：

  Prenylated derivatives of baicalein and 3,7-dihydroxyflavone: Synthesis and study of their effects on tumor cell lines growth, cell cycle and apoptosis

  摘要：

  Fourteen baicalein and 3,7-dihydroxyflavone derivatives were synthesized and evaluated for their inhibitory activity against the in vitro growth of three human tumor cell lines. The synthetic approaches were based on the reaction with prenyl or geranyl bromide in alkaline medium, followed by cyclization of the respective monoprenylated derivative. Dihydropyranoflavonoids were also obtained by one-pot synthesis, using Montmorillonite K10 clay as catalyst combined with microwave irradiation. In vitro screening of the compounds for cell growth inhibitory activity revealed that the presence of one geranyl group was associated with a remarkable increase in the inhibitory activity. Moreover, for the 3,7-dihydroxyflavone derivatives a marked increase in growth inhibitory effect was also observed for compounds with furan and pyran fused rings. The most active compounds were also studied regarding their effect on cell cycle profile and induction of apoptosis. Overall the results point to the relevant role of the prenylation of flavone scaffold in the growth inhibitory activity of cancer cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.047

文献信息

• Prenylated derivatives of baicalein and 3,7-dihydroxyflavone: Synthesis and study of their effects on tumor cell lines growth, cell cycle and apoptosis
  作者：Marta Perro Neves、Honorina Cidade、Madalena Pinto、Artur M.S. Silva、Luís Gales、Ana Margarida Damas、Raquel T. Lima、M. Helena Vasconcelos、Maria de São José Nascimento

  DOI：10.1016/j.ejmech.2011.03.047

  日期：2011.6

  Fourteen baicalein and 3,7-dihydroxyflavone derivatives were synthesized and evaluated for their inhibitory activity against the in vitro growth of three human tumor cell lines. The synthetic approaches were based on the reaction with prenyl or geranyl bromide in alkaline medium, followed by cyclization of the respective monoprenylated derivative. Dihydropyranoflavonoids were also obtained by one-pot synthesis, using Montmorillonite K10 clay as catalyst combined with microwave irradiation. In vitro screening of the compounds for cell growth inhibitory activity revealed that the presence of one geranyl group was associated with a remarkable increase in the inhibitory activity. Moreover, for the 3,7-dihydroxyflavone derivatives a marked increase in growth inhibitory effect was also observed for compounds with furan and pyran fused rings. The most active compounds were also studied regarding their effect on cell cycle profile and induction of apoptosis. Overall the results point to the relevant role of the prenylation of flavone scaffold in the growth inhibitory activity of cancer cells. (C) 2011 Elsevier Masson SAS. All rights reserved.