1,8-bis(2-bromobenzyloxy)-3-methylanthracene-9, 10-dione | 1612770-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-bis(2-bromobenzyloxy)-3-methylanthracene-9, 10-dione
• 英文别名: 1,8-Bis[(2-bromophenyl)methoxy]-3-methylanthracene-9,10-dione；1,8-bis[(2-bromophenyl)methoxy]-3-methylanthracene-9,10-dione
• CAS: 1612770-51-0
• 化学式: C₂₉H₂₀Br₂O₄
• 分子量: 592.283
• InChiKey: PDMVCMZQRBGRIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  大黄酚 、 1-溴-2-(碘甲基)苯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以80%的产率得到1,8-bis(2-bromobenzyloxy)-3-methylanthracene-9, 10-dione
  参考文献：
  名称：

  Synthesis, biological evaluation, molecular docking and theoretical evaluation of ADMET properties of nepodin and chrysophanol derivatives as potential cyclooxygenase (COX-1, COX-2) inhibitors

  摘要：

  Nepodin and chrysophanol, isolated from Rumex nepalensis roots, showed significant cyclooxygenase (COX) inhibitory activity. To further optimize these lead molecules and study structure activity relationship (SAR), eighteen derivatives of nepodin and nine derivatives of chrysophanol were synthesized and evaluated for COX-1 and COX-2 inhibitory potential. Among the synthesized compounds, four nepodin (1f, 1g, 1h and 1i) and three chrysophanol (2e, 2f and 2h) derivatives displayed more pronounced COX-2 inhibition than their respective lead molecule. Further, compounds 1f, 1g, 2e and 2h exhibited better anti-inflammatory activity than ibuprofen in carrageenan-induced rat paw edema assay. Taking into account the in vitro and in vivo results, molecular docking and in silico prediction of ADMET properties of compounds were carried out respectively.

  DOI：

  10.1016/j.ejmech.2014.04.033

文献信息

• Synthesis, biological evaluation, molecular docking and theoretical evaluation of ADMET properties of nepodin and chrysophanol derivatives as potential cyclooxygenase (COX-1, COX-2) inhibitors
  作者：Jagdeep Grover、Vivek Kumar、Vikram Singh、Khemraj Bairwa、M. Elizabeth Sobhia、Sanjay M. Jachak

  DOI：10.1016/j.ejmech.2014.04.033

  日期：2014.6

  Nepodin and chrysophanol, isolated from Rumex nepalensis roots, showed significant cyclooxygenase (COX) inhibitory activity. To further optimize these lead molecules and study structure activity relationship (SAR), eighteen derivatives of nepodin and nine derivatives of chrysophanol were synthesized and evaluated for COX-1 and COX-2 inhibitory potential. Among the synthesized compounds, four nepodin (1f, 1g, 1h and 1i) and three chrysophanol (2e, 2f and 2h) derivatives displayed more pronounced COX-2 inhibition than their respective lead molecule. Further, compounds 1f, 1g, 2e and 2h exhibited better anti-inflammatory activity than ibuprofen in carrageenan-induced rat paw edema assay. Taking into account the in vitro and in vivo results, molecular docking and in silico prediction of ADMET properties of compounds were carried out respectively.