3-bromo-4-octyloxybenzaldehyde | 101500-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-4-octyloxybenzaldehyde
• 英文别名: 3-bromo-4-octyloxy-benzaldehyde；3-Brom-4-octyloxy-benzaldehyd；3-Bromo-4-(octyloxy)benzaldehyde；3-bromo-4-octoxybenzaldehyde
• CAS: 101500-22-5
• 化学式: C₁₅H₂₁BrO₂
• mdl: MFCD18586003
• 分子量: 313.235
• InChiKey: CTEGLDYUDSIDAV-UHFFFAOYSA-N

物化性质

• 沸点：
  388.4±22.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-4-octyloxybenzaldehyde 在 ammonium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 ethyl 2-(3-cyano-4-octyloxyphenyl)-1-hydroxy-4-methyl-1H-imidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of 1-hydroxy/methoxy-4-methyl-2-phenyl-1H-imidazole-5-carboxylic acid derivatives as non-purine xanthine oxidase inhibitors

  摘要：

  Xanthine oxidase is a key enzyme that catalyses hypoxanthine and xanthine to uric acid, whose overproduction leads to the gout-causing hyperuricemia. In this study, a series of 1-hydroxy/methoxy-4-methy1-2-phenyl-1H-imidazole-5-carboxylic acid derivatives (4a-4k and 6a-6k) was synthesized and evaluated for their inhibitory potency against xanthine oxidase. The 1-hydroxyl substituted derivatives 4a-4k showed excellent inhibitory potency with IC50 values ranging from 0.003 mu M to 1.2 mu M, with compounds 4d (IC50 = 0.003 mu M), 4e (IC50 = 0.003 FM), and 4f (IC50 = 0.006 mu M) manifesting the most potent xanthine oxidase inhibitory potency that were comparable with that of Febuxostat (IC50 = 0.01 410). Lineweaver-Burk plot analysis revealed that representative compound 4f acted as a mixed-type inhibitor for xanthine oxidase. The basis of significant inhibition of xanthine oxidase by 4f was rationalized by its molecular docking into the active site of xanthine dehydrogenase. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.056
• 作为产物：
  描述：

  1-溴辛烷 、 3-溴-4-羟基苯甲醛 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以97.4%的产率得到3-bromo-4-octyloxybenzaldehyde
  参考文献：
  名称：

  Synthesis and evaluation of 1-hydroxy/methoxy-4-methyl-2-phenyl-1H-imidazole-5-carboxylic acid derivatives as non-purine xanthine oxidase inhibitors

  摘要：

  Xanthine oxidase is a key enzyme that catalyses hypoxanthine and xanthine to uric acid, whose overproduction leads to the gout-causing hyperuricemia. In this study, a series of 1-hydroxy/methoxy-4-methy1-2-phenyl-1H-imidazole-5-carboxylic acid derivatives (4a-4k and 6a-6k) was synthesized and evaluated for their inhibitory potency against xanthine oxidase. The 1-hydroxyl substituted derivatives 4a-4k showed excellent inhibitory potency with IC50 values ranging from 0.003 mu M to 1.2 mu M, with compounds 4d (IC50 = 0.003 mu M), 4e (IC50 = 0.003 FM), and 4f (IC50 = 0.006 mu M) manifesting the most potent xanthine oxidase inhibitory potency that were comparable with that of Febuxostat (IC50 = 0.01 410). Lineweaver-Burk plot analysis revealed that representative compound 4f acted as a mixed-type inhibitor for xanthine oxidase. The basis of significant inhibition of xanthine oxidase by 4f was rationalized by its molecular docking into the active site of xanthine dehydrogenase. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.056

文献信息

• Selecting against S1P3 enhances the acute cardiovascular tolerability of 3-(N-benzyl)aminopropylphosphonic acid S1P receptor agonists
  作者：Jeffrey J. Hale、George Doherty、Leslie Toth、Sander G. Mills、Richard Hajdu、Carol Ann Keohane、Mark Rosenbach、James Milligan、Gan-Ju Shei、Gary Chrebet、James Bergstrom、Deborah Card、Michael Forrest、Shu-Yu Sun、Sarah West、Huijuan Xie、Naomi Nomura、Hugh Rosen、Suzanne Mandala

  DOI：10.1016/j.bmcl.2004.04.070

  日期：2004.7

  Structurally modified 3-(N-benzylamino)propylphosphonic acid SIP receptor agonists that maintain affinity for S1P(1), and have decreased affinity for S1P(3) are efficacious, but exhibit decreased acute cardiovascular toxicity in rodents than do nonselective agonists. (C) 2004 Elsevier Ltd. All rights reserved.
• US7351725B2
  申请人：——

  公开号：US7351725B2

  公开（公告）日：2008-04-01
• Synthesis and evaluation of 1-hydroxy/methoxy-4-methyl-2-phenyl-1H-imidazole-5-carboxylic acid derivatives as non-purine xanthine oxidase inhibitors
  作者：Shaolei Chen、Tingjian Zhang、Jian Wang、Fangyang Wang、Handong Niu、Chunfu Wu、Shaojie Wang

  DOI：10.1016/j.ejmech.2015.08.056

  日期：2015.10

  Xanthine oxidase is a key enzyme that catalyses hypoxanthine and xanthine to uric acid, whose overproduction leads to the gout-causing hyperuricemia. In this study, a series of 1-hydroxy/methoxy-4-methy1-2-phenyl-1H-imidazole-5-carboxylic acid derivatives (4a-4k and 6a-6k) was synthesized and evaluated for their inhibitory potency against xanthine oxidase. The 1-hydroxyl substituted derivatives 4a-4k showed excellent inhibitory potency with IC50 values ranging from 0.003 mu M to 1.2 mu M, with compounds 4d (IC50 = 0.003 mu M), 4e (IC50 = 0.003 FM), and 4f (IC50 = 0.006 mu M) manifesting the most potent xanthine oxidase inhibitory potency that were comparable with that of Febuxostat (IC50 = 0.01 410). Lineweaver-Burk plot analysis revealed that representative compound 4f acted as a mixed-type inhibitor for xanthine oxidase. The basis of significant inhibition of xanthine oxidase by 4f was rationalized by its molecular docking into the active site of xanthine dehydrogenase. (C) 2015 Elsevier Masson SAS. All rights reserved.