(4-((4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)boronic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (4-((4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)boronic acid
• 英文别名: [4-[(4-Pyridin-2-yltriazol-1-yl)methyl]phenyl]boronic acid；[4-[(4-pyridin-2-yltriazol-1-yl)methyl]phenyl]boronic acid
• 化学式: C₁₄H₁₃BN₄O₂
• 分子量: 280.094
• InChiKey: ZKSMGNICWJQCDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(溴甲基)苯硼酸 在 sodium azide 、 cesium fluoride 、 copper(I) bromide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 26.0h， 生成 (4-((4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)boronic acid
  参考文献：
  名称：

  Boronic acid inhibitors of the class A β-lactamase KPC-2

  摘要：

  The rapid rise of antimicrobial resistance is one of the greatest challenges currently facing medical science. The most common cause of resistance to beta-lactam antibiotics is the expression of beta-lactamase enzymes, such as KPC-2. As such the development of novel inhibitors of KPC-2 and related enzymes is of the upmost importance. We report the design and synthesis of novel boronic acid transition state analogs containing a 1,4-substituted 1,2,3-triazole linker based on the known inhibitor 3-nitrophenyl boronic acid and demonstrate that they are promising scaffolds for the development inhibitors of KPC-2 with the ability to recover sensitivity to the antibiotic cefotaxime. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.04.055

文献信息

• Boronic acid inhibitors of the class A β-lactamase KPC-2
  作者：Jingyuan Zhou、Paul Stapleton、Shozeb Haider、Jess Healy

  DOI：10.1016/j.bmc.2018.04.055

  日期：2018.7

  The rapid rise of antimicrobial resistance is one of the greatest challenges currently facing medical science. The most common cause of resistance to beta-lactam antibiotics is the expression of beta-lactamase enzymes, such as KPC-2. As such the development of novel inhibitors of KPC-2 and related enzymes is of the upmost importance. We report the design and synthesis of novel boronic acid transition state analogs containing a 1,4-substituted 1,2,3-triazole linker based on the known inhibitor 3-nitrophenyl boronic acid and demonstrate that they are promising scaffolds for the development inhibitors of KPC-2 with the ability to recover sensitivity to the antibiotic cefotaxime. (C) 2018 Elsevier Ltd. All rights reserved.