(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)(3-chlorophenyl)methanone | 1346228-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-bromo-2-hydroxy-4,6-dimethoxyphenyl)(3-chlorophenyl)methanone
• 英文别名: (3-Bromo-2-hydroxy-4,6-dimethoxyphenyl)-(3-chlorophenyl)methanone；(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-(3-chlorophenyl)methanone
• CAS: 1346228-39-4
• 化学式: C₁₅H₁₂BrClO₄
• 分子量: 371.615
• InChiKey: UGAQLDFAPGIKFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-溴-2,4,6-三甲氧基苯 、 3-氯苯甲酰氯 在 aluminum (III) chloride 作用下， 以 乙醚 为溶剂， 反应 55.0h， 以43%的产率得到(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)(3-chlorophenyl)methanone
  参考文献：
  名称：

  Synthesis, biological evaluation, and pharmacokinetic profiling of benzophenone derivatives as tumor necrosis factor-alpha and interleukin-6 inhibitors

  摘要：

  A new series of benzophenone derivatives are reported with comparative less toxicity with qualifying pharmacokinetic profiles. They were synthesized by Fridel-Craft acylation and evaluated for their anti-inflammatory activity (against Tumor necrosis factor-alpha (TNF-alpha) and interleukin 6 (IL-6)) by LPS-induced cytokine production assay (phorbol myristate acetate stimulated human THP-1 cells in vitro). The screened compounds exhibited promising activity against IL-6 in a range of 63-82% at 10 mu M concentration. Cytotoxicity was also determined by using CCK-8 cells at 10 mu M. The synthesized benzophenone derivative 1c was not cytotoxic in CCK-8 cells up to the concentration of 100 mu M and showed potent IL-6 inhibitory activity with IC50 of 0.19 mu M. With few exceptions, all other compounds were found to be moderate inhibitors of TNF-alpha. In silico, pre-lead prioritization of the leads was performed using QikProp 3.2, qualifying them for further study.

  DOI：

  10.1007/s00044-011-9856-1

文献信息

• Synthesis, biological evaluation, and pharmacokinetic profiling of benzophenone derivatives as tumor necrosis factor-alpha and interleukin-6 inhibitors
  作者：Babasaheb Bandgar、Baliram Hote、Rahul Gangwal、Abhay Sangamwar

  DOI：10.1007/s00044-011-9856-1

  日期：2012.10

  A new series of benzophenone derivatives are reported with comparative less toxicity with qualifying pharmacokinetic profiles. They were synthesized by Fridel-Craft acylation and evaluated for their anti-inflammatory activity (against Tumor necrosis factor-alpha (TNF-alpha) and interleukin 6 (IL-6)) by LPS-induced cytokine production assay (phorbol myristate acetate stimulated human THP-1 cells in vitro). The screened compounds exhibited promising activity against IL-6 in a range of 63-82% at 10 mu M concentration. Cytotoxicity was also determined by using CCK-8 cells at 10 mu M. The synthesized benzophenone derivative 1c was not cytotoxic in CCK-8 cells up to the concentration of 100 mu M and showed potent IL-6 inhibitory activity with IC50 of 0.19 mu M. With few exceptions, all other compounds were found to be moderate inhibitors of TNF-alpha. In silico, pre-lead prioritization of the leads was performed using QikProp 3.2, qualifying them for further study.