acetic acid (3,5-dibromo-2,4-dihydroxy-benzylidene)-hydrazide | 1147839-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: acetic acid (3,5-dibromo-2,4-dihydroxy-benzylidene)-hydrazide
• CAS: 1147839-88-0
• 化学式: C₉H₈Br₂N₂O₃
• 分子量: 351.982
• InChiKey: ULSBJQOZEWDCET-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C
• 密度：
  2.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3,5-二溴-2,4-二羟基苯甲醛 、 乙酰肼 以 乙醇 为溶剂， 反应 3.0h， 以86.3%的产率得到acetic acid (3,5-dibromo-2,4-dihydroxy-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