3,5-dibromo-2,4-dimethoxy-benzaldehyde | 860725-02-6

• 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: 3,5-dibromo-2,4-dimethoxy-benzaldehyde
• 英文别名: 3,5-Dibrom-2,4-dimethoxy-benzaldehyd；3,5-Dibromo-2,4-dimethoxybenzaldehyde
• CAS: 860725-02-6
• 化学式: C₉H₈Br₂O₃
• 分子量: 323.969
• InChiKey: ZQWNNAAHCFHFOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-吡啶甲酰肼 、 3,5-dibromo-2,4-dimethoxy-benzaldehyde 以 乙醇 为溶剂， 反应 3.0h， 以61.8%的产率得到nicotinic acid (3,5-dibromo-2,4-dimethoxy-benzylidene)-hydrazide
  参考文献：
  名称：

  Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of Helicobacter pylori: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination

  摘要：

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.

  DOI：

  10.1021/jm8015602
• 作为产物：
  描述：

  3,5-二溴-2,4-二羟基苯甲醛 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以84.5%的产率得到3,5-dibromo-2,4-dimethoxy-benzaldehyde
  参考文献：
  名称：

  Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of Helicobacter pylori: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination

  摘要：

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.

  DOI：

  10.1021/jm8015602

文献信息

• Aerothionin and homoaerothionin: two tetrabromo spirocyclohexadienylisoxazoles from Verongia sponges
  作者：K. Moody、R. H. Thomson、E. Fattorusso、L. Minale、G. Sodano

  DOI：10.1039/p19720000018

  日期：——

  Aerothionin and homoaerothionin, tetrabromo-compounds from the sponges V. thiona and V. aerophoba are shown to be the homologous spirocyclohexadienylisoxazoles (XIII) and (XIV), respectively.

  来自海绵V. thiona和V. aerophoba的四溴代化合物Aerothionin和homaerothionin分别是同源的螺环己二烯基异恶唑（XIII）和（XIV）。
• CCXCIV.—Mercuration of some polyhydroxybenzaldehydes and their monomethyl ethers
  作者：Thomas Anderson Henry、Thomas Marvel Sharp

  DOI：10.1039/jr9300002279

  日期：——
• Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of <i>Helicobacter pylori</i>: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination
  作者：Lingyan He、Liang Zhang、Xiaofeng Liu、Xianghua Li、Mingyue Zheng、Honglin Li、Kunqian Yu、Kaixian Chen、Xu Shen、Hualiang Jiang、Hong Liu

  DOI：10.1021/jm8015602

  日期：2009.4.23

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.