5,7-Dimethoxy-2-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]chromen-4-one | 1407546-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5,7-Dimethoxy-2-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]chromen-4-one
• 英文别名: 5,7-dimethoxy-2-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]chromen-4-one
• CAS: 1407546-88-6
• 化学式: C₂₃H₂₆N₂O₅
• 分子量: 410.47
• InChiKey: MIUKJPQSUFWBKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  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

文献信息

• Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent
  作者：Girish D. Hatnapure、Ashish P. Keche、Atish H. Rodge、Satish S. Birajdar、Rajesh H. Tale、Vandana M. Kamble

  DOI：10.1016/j.bmcl.2012.08.071

  日期：2012.10

  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.