1-(2-hydroxy-3,4-dimethoxy-phenyl)-butane-1,3-dione | 65547-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxy-3,4-dimethoxy-phenyl)-butane-1,3-dione
• 英文别名: 1-(2-Hydroxy-3,4-dimethoxy-phenyl)-butan-1,3-dion；2-Hydroxy-3.4-dimethoxybenzoylaceton；1-(2-Hydroxy-3,4-dimethoxyphenyl)butane-1,3-dione
• CAS: 65547-75-3
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: XJYBXARVFMSRTG-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C
• 沸点：
  373.8±37.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-3,4-dimethoxy-phenyl)-butane-1,3-dione 在 盐酸 、 溶剂黄146 作用下， 生成 7,8-Dimethoxy-2-methyl-chromon
  参考文献：
  名称：

  Chromones in the Mannich Reaction

  摘要：

  DOI：

  10.1021/ja01137a024
• 作为产物：
  描述：

  2'-羟基-3',4'-二甲氧基苯乙酮 、 乙酸乙酯 在 sodium 作用下， 反应 18.0h， 生成 1-(2-hydroxy-3,4-dimethoxy-phenyl)-butane-1,3-dione
  参考文献：
  名称：

  Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells

  摘要：

  A series of 2-styrylchromone analogs were synthesized and examined for their antiproliferative effects on a panel of carcinoma cells. Among the tested agents, only 4m exhibited a moderate activity with an IC(50) value of 28.9 mu M against PC-3 cells which indicates the selectivity of PC-3 cells in response to 2-styrylchromones. In addition, 4q demonstrated the most antiproliferative effect with an IC50 value of 4.9 mu M against HeLa cells. Flow cytometric analysis and DAPI staining revealed that HeLa cells exposed to 4q as low as 5 mu M induced cell death through sub-G1 arrest and DNA fragmentation. Furthermore, CoMFA analysis of tested 2-styrylchromones resulted in a q(2) of 0.459 to generate a 3D-QSAR model on BT483 cell line. Together, these results suggest a potential structural optimization and pharmacological study of 2-styrylchromones. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.034

文献信息

• Chromones in the Mannich Reaction
  作者：Paul F. Wiley

  DOI：10.1021/ja01137a024

  日期：1952.9
• AHLUWALIA V. K.; KUMAR D., INDIAN J. CHEM., 1977, B 15, NO 6, 514-518
  作者：AHLUWALIA V. K.、 KUMAR D.

  DOI：——

  日期：——
• Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells
  作者：Arthur Y. Shaw、Chun-Yi Chang、Hao-Han Liau、Pei-Jung Lu、Hui-Ling Chen、Chia-Ning Yang、Hao-Yi Li

  DOI：10.1016/j.ejmech.2009.01.034

  日期：2009.6

  A series of 2-styrylchromone analogs were synthesized and examined for their antiproliferative effects on a panel of carcinoma cells. Among the tested agents, only 4m exhibited a moderate activity with an IC(50) value of 28.9 mu M against PC-3 cells which indicates the selectivity of PC-3 cells in response to 2-styrylchromones. In addition, 4q demonstrated the most antiproliferative effect with an IC50 value of 4.9 mu M against HeLa cells. Flow cytometric analysis and DAPI staining revealed that HeLa cells exposed to 4q as low as 5 mu M induced cell death through sub-G1 arrest and DNA fragmentation. Furthermore, CoMFA analysis of tested 2-styrylchromones resulted in a q(2) of 0.459 to generate a 3D-QSAR model on BT483 cell line. Together, these results suggest a potential structural optimization and pharmacological study of 2-styrylchromones. (C) 2009 Elsevier Masson SAS. All rights reserved.