1-(2-hydroxy-4, 6-dimethoxyphenyl)butane-1,3-dione | 65547-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxy-4, 6-dimethoxyphenyl)butane-1,3-dione
• 英文别名: 1-(2-hydroxy-4,6-dimethoxy-phenyl)-butane-1,3-dione；1-(2-Hydroxy-4,6-dimethoxy-phenyl)-butan-1,3-dion；2-Hydroxy-4.6-dimethoxy-benzoylaceton；1-(2-Hydroxy-4,6-dimethoxyphenyl)-1,3-butanedione；1-(2-hydroxy-4,6-dimethoxyphenyl)butane-1,3-dione
• CAS: 65547-60-6
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: HSRZGMDZNNYWBS-UHFFFAOYSA-N

物化性质

• 熔点：
  82 °C
• 沸点：
  417.1±40.0 °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-4, 6-dimethoxyphenyl)butane-1,3-dione 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 22.5h， 生成 5,7-Dimethoxy-2-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

  摘要：

  A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-alpha and 70-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 mu M) while the compounds5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.071
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 乙酸乙酯 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 48.0h， 生成 1-(2-hydroxy-4, 6-dimethoxyphenyl)butane-1,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

  摘要：

  A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-alpha and 70-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 mu M) while the compounds5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.071

文献信息

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

  DOI：10.1021/ja01137a024

  日期：1952.9
• Mackenzie et al., Journal of the Chemical Society, 1950, p. 2965,2969
  作者：Mackenzie et al.

  DOI：——

  日期：——
• 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：——