(E)-3-(2,6-dichlorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one | 1424351-75-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(2,6-dichlorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-(3-nitrophenyl)prop-2-en-1-one；(E)-1-[2-hydroxy-4,6-dimethoxy-3-(2-methylpyrazol-3-yl)phenyl]-3-(3-nitrophenyl)prop-2-en-1-one
• CAS: 1424351-75-6
• 化学式: C₂₁H₁₉N₃O₆
• 分子量: 409.398
• InChiKey: ZTWPVDWDLKWYPH-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,6-dichlorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 5,7-Dimethoxy-8-(2-methylpyrazol-3-yl)-2-(3-nitrophenyl)chromen-4-one
  参考文献：
  名称：

  Design, synthesis, characterization and anti-inflammatory evaluation of novel pyrazole amalgamated flavones

  摘要：

  A series of novel pyrazole amalgamated flavones has been designed and synthesized from 1-methyl-5-(2,4,6-trimethoxy-phenyl)-1H-pyrazole 6. The structures of regioisomers 6 and 7 were resolved by 2D H-1-H-1 COSY, H-1-C-13 HSQC and H-1-C-13 HMBC experiments. The newly synthesized compounds were tested for their in vitro COX inhibition and in vivo carrageenan induced hind paw edema in rats and acetic acid induced vascular permeability in mice. Although the compounds have inhibitory profile against both COX-1 and COX-2, some of the compounds are found to be selective against COX-2, supported by inhibition of paw edema and vascular permeability. Docking studies were also carried out to determine the structural features which sway the anti-inflammatory activity of the tested compounds. The keto and phenolic -OH are major factors that are prominently involved in interaction with COX-2 active site. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.094
• 作为产物：
  描述：

  3-oxo-3-(2,4,6-trimethoxyphenyl)propanal 在 三氟化硼乙醚 、 sodium hydride 、 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.75h， 生成 (E)-3-(2,6-dichlorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

  摘要：

  A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D H-1-H-1 COSY, H-1-C-13 HSQC and H-1-C-13 HMBC experiments. The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e, 10f, and 10h were found to be potent anti-inflammatory agents.

  DOI：

  10.3109/14756366.2013.873037