1-(2-(dodecyloxy)-4-methoxyphenyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(dodecyloxy)-4-methoxyphenyl)ethanone
• 英文别名: 1-(2-Dodecoxy-4-methoxyphenyl)ethanone；1-(2-dodecoxy-4-methoxyphenyl)ethanone
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: DBLAWUQBPXNJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丹皮酚 、 溴代十二烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 以55.4%的产率得到1-(2-(dodecyloxy)-4-methoxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of paeonol analogues in the murine model of complete Freund’s adjuvant induced arthritis

  摘要：

  A new series of paeonol alkyl ether analogues were synthesized and confirmed with IR, H-1 NMR, C-13 NMR and HRMS spectra. They have shown anti-inflammatory activities by scavenging mediator of free radicals and inhibiting lipid mediator of inflammation on complete Freund's adjuvant (CFA) induced arthritis in mice. The in vitro and in vivo scavenging ability of free radicals was determined by using chemical analysis and commercial assay kits, respectively. The in vivo inhibiting lipid mediator of inflammation was examined by ELISA. Our results indicated that the substitution of the hydrogen in hydroxyl group at C2 position of paeonol 1 by short carbon chain, in the presence or absence of bromo atom at C5 position, decreased its scavenging ability on radicals (3a or 4a vs 1), while the long alkyl substitution (C >14) increased the activity. Compared with 3a or 4a, scavenging abilities of 3a-h or 4a-h gradually increased following the length elongation of alkyl carbon chain. Compounds 3h and 4h showed great scavenging ability on OH, O-2(-), DPPH, ATBS' and MDA, and good promotion on T-AOC and SOD. The results of the in vivo inhibiting lipid mediator of inflammation also demonstrated that 3h, 4h exhibited substantial inhibition on enzyme activity of COX-2, PGE2. Therefore, 3h and 4h have great potential to be the novel anti-inflammatory drug candidates for the therapy of arthritis. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.09.060

文献信息

• Synthesis and anti-inflammatory activity of paeonol analogues in the murine model of complete Freund’s adjuvant induced arthritis
  作者：Ligua Huang、Baoshun Zhang、You Yang、Xiaobao Gong、Zhu Chen、Zhenxu Wang、Peng Zhang、Qingyan Zhang

  DOI：10.1016/j.bmcl.2016.09.060

  日期：2016.11

  A new series of paeonol alkyl ether analogues were synthesized and confirmed with IR, H-1 NMR, C-13 NMR and HRMS spectra. They have shown anti-inflammatory activities by scavenging mediator of free radicals and inhibiting lipid mediator of inflammation on complete Freund's adjuvant (CFA) induced arthritis in mice. The in vitro and in vivo scavenging ability of free radicals was determined by using chemical analysis and commercial assay kits, respectively. The in vivo inhibiting lipid mediator of inflammation was examined by ELISA. Our results indicated that the substitution of the hydrogen in hydroxyl group at C2 position of paeonol 1 by short carbon chain, in the presence or absence of bromo atom at C5 position, decreased its scavenging ability on radicals (3a or 4a vs 1), while the long alkyl substitution (C >14) increased the activity. Compared with 3a or 4a, scavenging abilities of 3a-h or 4a-h gradually increased following the length elongation of alkyl carbon chain. Compounds 3h and 4h showed great scavenging ability on OH, O-2(-), DPPH, ATBS' and MDA, and good promotion on T-AOC and SOD. The results of the in vivo inhibiting lipid mediator of inflammation also demonstrated that 3h, 4h exhibited substantial inhibition on enzyme activity of COX-2, PGE2. Therefore, 3h and 4h have great potential to be the novel anti-inflammatory drug candidates for the therapy of arthritis. (C) 2016 Elsevier Ltd. All rights reserved.