3-(2-hydroxynaphthalen-1-ylazo)phenylboronic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2-hydroxynaphthalen-1-ylazo)phenylboronic acid
• 英文别名: 3-(2-Hydroxy-naphthalen-1-ylazo)-phenyl-boronic acid；[3-[(2-hydroxynaphthalen-1-yl)diazenyl]phenyl]boronic acid
• 化学式: C₁₆H₁₃BN₂O₃
• 分子量: 292.102
• InChiKey: ATAKVTSBJMUNSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氨基苯硼酸 、 2-萘酚 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 生成 3-(2-hydroxynaphthalen-1-ylazo)phenylboronic acid
  参考文献：
  名称：

  Aza-boronic acids as non-β-lactam inhibitors of AmpC-β-lactamase

  摘要：

  With the aim of improving the ability of non-p-lactam inhibitors to inhibit AmpC-beta-tactamase, a series of 3-aza-phenyl-boronic acid derivatives was obtained using in parallel synthesis. The molecules were tested against Escherichia coli AmpC-beta-lactamase. The best inhibitors, 3-(2-hydroxy-naphthalen-1-ylazo)-phenyl-boronic acid (12) and 3-(2,4-dihydroxy-naphthalen-1-ylazo)-phenyl-boronic acid (14), showed apparent inhibition constant values (K-i) of 0.3 and 0.45 muM and increased the potency of the semi-synthetic cephalosporin antibiotic, ceftazidime, lowering its minimum inhibitory concentration (MIC) value of 50%, against Gram-negative bacteria strains, producing high levels of AmpC-p-lactamase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.054

文献信息

• Aza-boronic acids as non-β-lactam inhibitors of AmpC-β-lactamase
  作者：Valentina Buzzoni、Jesus Blazquez、Stefania Ferrari、Samuele Calò、Alberto Venturelli、M.Paola Costi

  DOI：10.1016/j.bmcl.2004.05.054

  日期：2004.8

  With the aim of improving the ability of non-p-lactam inhibitors to inhibit AmpC-beta-tactamase, a series of 3-aza-phenyl-boronic acid derivatives was obtained using in parallel synthesis. The molecules were tested against Escherichia coli AmpC-beta-lactamase. The best inhibitors, 3-(2-hydroxy-naphthalen-1-ylazo)-phenyl-boronic acid (12) and 3-(2,4-dihydroxy-naphthalen-1-ylazo)-phenyl-boronic acid (14), showed apparent inhibition constant values (K-i) of 0.3 and 0.45 muM and increased the potency of the semi-synthetic cephalosporin antibiotic, ceftazidime, lowering its minimum inhibitory concentration (MIC) value of 50%, against Gram-negative bacteria strains, producing high levels of AmpC-p-lactamase. (C) 2004 Elsevier Ltd. All rights reserved.