2-(4-Bromophenyl)-5,7-dimethoxy-8-(2-methylpyrazol-3-yl)chromen-4-one | 1424351-88-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-Bromophenyl)-5,7-dimethoxy-8-(2-methylpyrazol-3-yl)chromen-4-one
• 英文别名: 2-(4-bromophenyl)-5,7-dimethoxy-8-(2-methylpyrazol-3-yl)chromen-4-one
• CAS: 1424351-88-1
• 化学式: C₂₁H₁₇BrN₂O₄
• 分子量: 441.281
• InChiKey: IKYFHDQEEZNMFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 在 三氟化硼乙醚 、 碘 、 sodium hydride 、 potassium carbonate 、 一水合肼 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 65.0h， 生成 2-(4-Bromophenyl)-5,7-dimethoxy-8-(2-methylpyrazol-3-yl)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

文献信息

• Design, synthesis, characterization and anti-inflammatory evaluation of novel pyrazole amalgamated flavones
  作者：Hemant V. Chavan、Babasaheb P. Bandgar、Laxman K. Adsul、Valmik D. Dhakane、Pravin S. Bhale、Vishnu N. Thakare、Vijay Masand

  DOI：10.1016/j.bmcl.2012.12.094

  日期：2013.3

  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.