3-(3-(2-hydroxyphenyl)-3-oxopropyl)-4H-chromen-4-one | 52853-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-(2-hydroxyphenyl)-3-oxopropyl)-4H-chromen-4-one
• 英文别名: 1-(3-Chromonyl)-2-salicyloyl-ethan；3-[3-(2-hydroxy-phenyl)-3-oxo-propyl]-chromen-4-one
• CAS: 52853-00-6
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: NXDHHMFJEUJWBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.51
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(3-(2-hydroxyphenyl)-3-oxopropyl)-4H-chromen-4-one 、 N,N-二甲基甲酰胺 在 三氟化硼乙醚 、 甲基磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以54%的产率得到di(4-oxo-4H-1-benzopyran-3-yl)methane
  参考文献：
  名称：

  Synthesis and SAR studies of bis-chromenone derivatives for anti-proliferative activity against human cancer cells

  摘要：

  A novel family of 3-((4-oxo-4H-chromen-3-yl)methyl)-4H-chromen-4-one (bis-chromone) derivatives were designed, synthesized and studied for their anti-cancer activity using the XTT assay for the growth inhibition against various human cancer cells. Among them, 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-methoxy-4H-chromen-4-one and 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-hydroxy-4H-chromen-4-one showed micromolar level of in vitro anti-proliferative activity against human cancer cell lines. The SAR studies indicated bis-chromone as a basic scaffold to design anticancer agents. The 5-cyclohexylmethoxy on the first chromenone ring and electron donating group such as CH3, OCH3 or hydrogen bonding group (OH) on the other chromenone ring of bis-chromone increased the activity. However, saturation of one of chromenone to chromanone in bis-chromones decreased the activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.057
• 作为产物：
  描述：

  色酮-3-甲醛 在 palladium on carbon 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-(3-(2-hydroxyphenyl)-3-oxopropyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and SAR studies of bis-chromenone derivatives for anti-proliferative activity against human cancer cells

  摘要：

  A novel family of 3-((4-oxo-4H-chromen-3-yl)methyl)-4H-chromen-4-one (bis-chromone) derivatives were designed, synthesized and studied for their anti-cancer activity using the XTT assay for the growth inhibition against various human cancer cells. Among them, 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-methoxy-4H-chromen-4-one and 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-hydroxy-4H-chromen-4-one showed micromolar level of in vitro anti-proliferative activity against human cancer cell lines. The SAR studies indicated bis-chromone as a basic scaffold to design anticancer agents. The 5-cyclohexylmethoxy on the first chromenone ring and electron donating group such as CH3, OCH3 or hydrogen bonding group (OH) on the other chromenone ring of bis-chromone increased the activity. However, saturation of one of chromenone to chromanone in bis-chromones decreased the activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.057