3-(3-Bromo-4-formylphenoxy)-4-methylbenzonitrile | 1426224-08-9

• 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-(3-Bromo-4-formylphenoxy)-4-methylbenzonitrile
• 英文别名: 3-(3-bromo-4-formylphenoxy)-4-methylbenzonitrile
• CAS: 1426224-08-9
• 化学式: C₁₅H₁₀BrNO₂
• 分子量: 316.154
• InChiKey: SONPXVNUDNODJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-Bromo-4-formylphenoxy)-4-methylbenzonitrile 在 盐酸 、 sodium tetrahydroborate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 3-[(1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]-4-methylbenzonitrile
  参考文献：
  名称：

  Structure–activity relationships of 6-(aminomethylphenoxy)-benzoxaborole derivatives as anti-inflammatory agent

  摘要：

  A series of novel 6-(aminomethylphenoxy)benzoxaborole analogs was synthesized for the investigation of the structure-activity relationship of the inhibition of TNF-alpha, IL-1beta, and IL-6, from lipopolysaccharide stimulated peripheral blood mononuclear cells. Compounds 9d and 9e showed potent activity against all three cytokines with IC50 values between 33 and 83 nM. Chloro substituted analog 9e (AN3485) is considered to be a promising lead for novel anti-inflammatory agent with a favorable pharmacokinetic profile. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.072
• 作为产物：
  描述：

  2-溴-4-氟苯甲醛 、 3-羟基-4-甲基苯腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(3-Bromo-4-formylphenoxy)-4-methylbenzonitrile
  参考文献：
  名称：

  Structure–activity relationships of 6-(aminomethylphenoxy)-benzoxaborole derivatives as anti-inflammatory agent

  摘要：

  A series of novel 6-(aminomethylphenoxy)benzoxaborole analogs was synthesized for the investigation of the structure-activity relationship of the inhibition of TNF-alpha, IL-1beta, and IL-6, from lipopolysaccharide stimulated peripheral blood mononuclear cells. Compounds 9d and 9e showed potent activity against all three cytokines with IC50 values between 33 and 83 nM. Chloro substituted analog 9e (AN3485) is considered to be a promising lead for novel anti-inflammatory agent with a favorable pharmacokinetic profile. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.072

文献信息

• Structure–activity relationships of 6-(aminomethylphenoxy)-benzoxaborole derivatives as anti-inflammatory agent
  作者：Tsutomu Akama、Charlotte Virtucio、Chen Dong、Richard Kimura、Yong-Kang Zhang、James A. Nieman、Rashmi Sharma、Xiaosong Lu、Marcelo Sales、Rajeshwar Singh、Anne Wu、Xiao-Qing Fan、Liang Liu、Jacob J. Plattner、Kurt Jarnagin、Yvonne R. Freund

  DOI：10.1016/j.bmcl.2013.01.072

  日期：2013.3

  A series of novel 6-(aminomethylphenoxy)benzoxaborole analogs was synthesized for the investigation of the structure-activity relationship of the inhibition of TNF-alpha, IL-1beta, and IL-6, from lipopolysaccharide stimulated peripheral blood mononuclear cells. Compounds 9d and 9e showed potent activity against all three cytokines with IC50 values between 33 and 83 nM. Chloro substituted analog 9e (AN3485) is considered to be a promising lead for novel anti-inflammatory agent with a favorable pharmacokinetic profile. (C) 2013 Elsevier Ltd. All rights reserved.