2-(bromomethyl)-5, 7-dimethoxy-4H-chromen-4-one | 1407546-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(bromomethyl)-5, 7-dimethoxy-4H-chromen-4-one
• 英文别名: 2-(Bromomethyl)-5,7-dimethoxychromen-4-one；2-(bromomethyl)-5,7-dimethoxychromen-4-one
• CAS: 1407546-86-4
• 化学式: C₁₂H₁₁BrO₄
• 分子量: 299.121
• InChiKey: QZHNBBFZNGVILY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙基哌嗪 、 2-(bromomethyl)-5, 7-dimethoxy-4H-chromen-4-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以66%的产率得到2-[(4-Ethylpiperazin-1-yl)methyl]-5,7-dimethoxychromen-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：

  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 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 水 为溶剂， 反应 6.5h， 生成 2-(bromomethyl)-5, 7-dimethoxy-4H-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